SK1642003A3 - Process of separating a single desired stereoisomer from a racemic mixture - Google Patents

Process of separating a single desired stereoisomer from a racemic mixture Download PDF

Info

Publication number: SK1642003A3
Authority: SK; Slovakia
Prior art keywords: compound; lipase; formula; process according; group
Prior art date: 2000-07-07

Application number

SK164-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Jennifer Ann Chaplin

Neil Stockenstrom Gardiner

Robin Kumar Mitra

Christopher John Parkinson

Madrie Portwig

Butana Andrew Mboniswa

Melanie Daryl Evans-Dickson

Dean Brady

Stephanus Francois Marais

Shavani Reddy

Original Assignee

Csir

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-07-07

Filing date

2001-06-11

Publication date

2003-08-05

2001-06-11 Application filed by Csir filed Critical Csir

2003-08-05 Publication of SK1642003A3 publication Critical patent/SK1642003A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 47
239000000203 mixture Substances 0.000 title claims abstract description 34
150000001875 compounds Chemical class 0.000 claims abstract description 81
102000004190 Enzymes Human genes 0.000 claims abstract description 45
108090000790 Enzymes Proteins 0.000 claims abstract description 45
238000006243 chemical reaction Methods 0.000 claims abstract description 31
239000007795 chemical reaction product Substances 0.000 claims abstract description 31
239000003795 chemical substances by application Substances 0.000 claims abstract description 22
239000003960 organic solvent Substances 0.000 claims abstract description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 16
230000000707 stereoselective effect Effects 0.000 claims abstract description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 10
239000006227 byproduct Substances 0.000 claims abstract description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
102000004882 Lipase Human genes 0.000 claims description 33
108090001060 Lipase Proteins 0.000 claims description 33
239000004367 Lipase Substances 0.000 claims description 33
235000019421 lipase Nutrition 0.000 claims description 33
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 32
239000002904 solvent Substances 0.000 claims description 22
239000003054 catalyst Substances 0.000 claims description 21
239000000725 suspension Substances 0.000 claims description 11
108090000371 Esterases Proteins 0.000 claims description 10
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
241001661345 Moesziomyces antarcticus Species 0.000 claims description 8
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
108010013563 Lipoprotein Lipase Proteins 0.000 claims description 7
239000000047 product Substances 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
102000043296 Lipoprotein lipases Human genes 0.000 claims description 6
-1 Novozyme 868 Proteins 0.000 claims description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
240000006439 Aspergillus oryzae Species 0.000 claims description 5
235000002247 Aspergillus oryzae Nutrition 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
108091005804 Peptidases Proteins 0.000 claims description 4
102000035195 Peptidases Human genes 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
229940116333 ethyl lactate Drugs 0.000 claims description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
235000019833 protease Nutrition 0.000 claims description 4
241000589513 Burkholderia cepacia Species 0.000 claims description 3
108010073038 Penicillin Amidase Proteins 0.000 claims description 3
241000589774 Pseudomonas sp. Species 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
241001453380 Burkholderia Species 0.000 claims description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
102000013392 Carboxylesterase Human genes 0.000 claims description 2
108010051152 Carboxylesterase Proteins 0.000 claims description 2
241000146387 Chromobacterium viscosum Species 0.000 claims description 2
241000222175 Diutina rugosa Species 0.000 claims description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 claims description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
108010084311 Novozyme 435 Proteins 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
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240000000064 Penicillium roqueforti Species 0.000 claims description 2
235000002233 Penicillium roqueforti Nutrition 0.000 claims description 2
101001003495 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 2
101001064559 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 2
241000235403 Rhizomucor miehei Species 0.000 claims description 2
101000968489 Rhizomucor miehei Lipase Proteins 0.000 claims description 2
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101000966371 Rhizopus niveus Lipase Proteins 0.000 claims description 2
241000179532 [Candida] cylindracea Species 0.000 claims description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 claims description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 2
210000003918 fraction a Anatomy 0.000 claims description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
239000003350 kerosene Substances 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
241000235395 Mucor Species 0.000 claims 2
241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
241000193385 Geobacillus stearothermophilus Species 0.000 claims 1
241001139947 Mida Species 0.000 claims 1
241000498617 Mucor javanicus Species 0.000 claims 1
240000005384 Rhizopus oryzae Species 0.000 claims 1
235000013752 Rhizopus oryzae Nutrition 0.000 claims 1
210000001015 abdomen Anatomy 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 abstract description 41
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract description 32
229960004873 levomenthol Drugs 0.000 abstract description 9
229940041616 menthol Drugs 0.000 description 21
MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 14
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
239000005844 Thymol Substances 0.000 description 7
229960000790 thymol Drugs 0.000 description 7
XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000004064 recycling Methods 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
244000005700 microbiome Species 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
108010093096 Immobilized Enzymes Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000032050 esterification Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
230000006340 racemization Effects 0.000 description 3
229940075966 (+)- menthol Drugs 0.000 description 2
NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000193830 Bacillus <bacterium> Species 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
108010056079 Subtilisins Proteins 0.000 description 2
102000005158 Subtilisins Human genes 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003518 caustics Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012374 esterification agent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 2
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000010457 zeolite Substances 0.000 description 2
NOOLISFMXDJSKH-LPEHRKFASA-N (1r,2s,5s)-5-methyl-2-propan-2-ylcyclohexan-1-ol Chemical compound CC(C)[C@@H]1CC[C@H](C)C[C@H]1O NOOLISFMXDJSKH-LPEHRKFASA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
XHXUANMFYXWVNG-UHFFFAOYSA-N D-menthyl acetate Natural products CC(C)C1CCC(C)CC1OC(C)=O XHXUANMFYXWVNG-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000589540 Pseudomonas fluorescens Species 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
241000235015 Yarrowia lipolytica Species 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
XHXUANMFYXWVNG-WCQGTBRESA-N [(1s,2r,5s)-5-methyl-2-propan-2-ylcyclohexyl] acetate Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1OC(C)=O XHXUANMFYXWVNG-WCQGTBRESA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
235000019504 cigarettes Nutrition 0.000 description 1
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(II) oxide Inorganic materials [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
239000008368 mint flavor Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000000606 toothpaste Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK164-2003A 2000-07-07 2001-06-11 Process of separating a single desired stereoisomer from a racemic mixture SK1642003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ZA200003417		2000-07-07
PCT/IB2001/001008 WO2002004384A2 (en)	2000-07-07	2001-06-11	Process for preparing (-)menthol and similar compounds

Publications (1)

Publication Number	Publication Date
SK1642003A3 true SK1642003A3 (en)	2003-08-05

Family

ID=25588814

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK164-2003A SK1642003A3 (en)	2000-07-07	2001-06-11	Process of separating a single desired stereoisomer from a racemic mixture

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KR100846674B1 (ko)	2006-03-10	2008-07-16	엔자이텍 주식회사	효소적 방법에 의한 광학활성 트랜스 알코올 화합물 및 그의 에스테르 화합물 제조방법
WO2010095034A1 (en)	2009-02-17	2010-08-26	Nagaoka & Co., Ltd.	Methods and apparatus for production of natural l-menthol
CN104177233B (zh) *	2014-09-10	2015-10-28	湖南湘易康制药有限公司	一种麝香草酚的合成方法
CN104311392A (zh) *	2014-10-12	2015-01-28	王同俊	R-1-(3,4-二甲基苯基)乙醇及其酯的合成
CN104311393A (zh) *	2014-10-12	2015-01-28	王同俊	一种r-1-(3-氯苯基)乙醇及其酯的制备方法
CN106380408A (zh) *	2016-09-04	2017-02-08	王际菊	一种光学纯手性胺的制备方法
CN106397225A (zh) *	2016-09-04	2017-02-15	王际菊	一种手性化合物的制备方法

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DE538376C (de)	1930-12-11	1931-11-14	Oscar Hinsberg Dr	Verfahren zur Kernalkylierung von Phenolen und Phenolaethern sowie deren Kern-Substitutionsprodukten
JP3289058B2 (ja) *	1992-09-11	2002-06-04	工業技術院長	酵素を用いたエステル製造方法
DE60101509T2 (de) *	2000-06-19	2004-10-14	Loders Croklaan B.V.	Cla-ester

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WO2002004384A3 (en)	2002-06-20
US7026144B2 (en)	2006-04-11
EP1301452A2 (en)	2003-04-16
US20030153031A1 (en)	2003-08-14
CZ2003285A3 (cs)	2003-10-15
BR0112501A (pt)	2003-07-29
AU7864001A (en)	2002-01-21
CN1452603A (zh)	2003-10-29
WO2002004384A2 (en)	2002-01-17
JP2004502744A (ja)	2004-01-29
AU2001278640B2 (en)	2006-04-13
RU2286331C2 (ru)	2006-10-27
CN1240646C (zh)	2006-02-08
MXPA02012645A (es)	2004-09-10

Publication	Publication Date	Title
SK1642003A3 (en)	2003-08-05	Process of separating a single desired stereoisomer from a racemic mixture
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