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NO138948B - METHOD FOR EXTRACTING D-PENICILLAMINE - Google Patents

METHOD FOR EXTRACTING D-PENICILLAMINE Download PDF

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Publication number
NO138948B
NO138948B NO3693/73A NO369373A NO138948B NO 138948 B NO138948 B NO 138948B NO 3693/73 A NO3693/73 A NO 3693/73A NO 369373 A NO369373 A NO 369373A NO 138948 B NO138948 B NO 138948B
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Prior art keywords
acid
penicillamine
norephedrine
formyl
mol
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NO3693/73A
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Norwegian (no)
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NO138948C (en
Inventor
Friedrich Asinger
Heribert Offermanns
Karl-Heinz Gluzek
Walter Von Bebenburg
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Degussa
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Publication of NO138948B publication Critical patent/NO138948B/en
Publication of NO138948C publication Critical patent/NO138948C/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Description

Oppfinnelsen vedrører fremgangsmåte til utvinning av D-penicillamin fra D,L-penicillamin ifølge patent nr. 135.903. The invention relates to a method for extracting D-penicillamine from D,L-penicillamine according to patent no. 135,903.

Det er funnet at det er spesielt fordelaktig ved utvinning av D-penicillamin av D,L-penicillamin ifølge patent nr. 135-903 at den anvendte base er 1-norefedrin som anvendes som salt. It has been found that it is particularly advantageous when extracting D-penicillamine from D,L-penicillamine according to patent no. 135-903 that the base used is 1-norephedrine which is used as a salt.

1-norefedrin fremkommer vanligvis ved dets fremstilling i form av salter. Idet disse salter umiddelbart anvendes ved anvendelsen av 1-norefedrin til fremstilling av D-penicillamin inn spares frembringelsen av norefedrinets fri base. 1-norephedrine is usually produced in the form of salts. Since these salts are immediately used when using 1-norephedrine for the production of D-penicillamine, the production of norephedrine's free base is saved.

Som salter av 1-norefedrin kommer det spesielt på As salts of 1-norephedrine, it comes in particular

tale salter med organiske syrer, spesielt med sulfonsyre og spesielt med karboksylsyre. Ved sulfonsyrene dreier det seg eksem-pelvis om alifatiske sulfonsyrer som metansulfonsyre, metantrisul-fonsyre og propan-2-sulfonsyre, eller om aromatiske"sulfonsyrer som p-toluensulfonsyre, spesielt om benzensulfonsyre. Blant kar-boksylsyrene er mettede eller umettede, eventuelt med 0H-, NI^-, NHR-, NR2-, OR-, SH-, SR- eller halogengrupper substituerte, alifatiske mono- og polykarboksylsyrer, som isosmørsyre, N-valerian-syre, isovaleriansyre, trimetyleddiksyre, melkesyre, oksalsyre, malonsyre, adipinsyre, maleinsyre, ravsyre, vinsyre, sitronsyre, spesielt slike med 1 til 6 karbonatomer, som maursyre, eddik-syre, propionsyre eller aralifatiske karboksylsyrer, som fenyl-eddiksyre, mandelsyre, kanelsyre, spesielt 3-fenyl-propionsyre eller aromatiske karboksylsyrer som ftalsyre, tereftalsyre, salicylsyre, spesielt 3-fenyl-propionsyre eller aromatiske karbok- say salts with organic acids, especially with sulphonic acid and especially with carboxylic acid. The sulfonic acids are, for example, aliphatic sulfonic acids such as methanesulfonic acid, methanetrisulfonic acid and propane-2-sulfonic acid, or aromatic "sulfonic acids" such as p-toluenesulfonic acid, especially benzenesulfonic acid. Among the carboxylic acids are saturated or unsaturated, possibly with OH -, NI^-, NHR-, NR2-, OR-, SH-, SR- or halogen group substituted, aliphatic mono- and polycarboxylic acids, such as isobutyric acid, N-valeric acid, isovaleric acid, trimethylacetic acid, lactic acid, oxalic acid, malonic acid, adipic acid , maleic acid, succinic acid, tartaric acid, citric acid, especially those with 1 to 6 carbon atoms, such as formic acid, acetic acid, propionic acid or araliphatic carboxylic acids, such as phenylacetic acid, mandelic acid, cinnamic acid, especially 3-phenylpropionic acid or aromatic carboxylic acids such as phthalic acid, terephthalic acid, salicylic acid, especially 3-phenyl-propionic acid or aromatic carboxy-

sylsyrer som ftalsyre, tereftalsyre, salicylsyre, spesielt benzosyre eller heteroaromatiske karboksylsyrer, som tiofen-2-karboksylsyre, tiazol-4-karboksylsyre, furan-2-karboksylsyre, picolinsyre, isonikotinsyre. syllic acids such as phthalic acid, terephthalic acid, salicylic acid, especially benzoic acid or heteroaromatic carboxylic acids, such as thiophene-2-carboxylic acid, thiazole-4-carboxylic acid, furan-2-carboxylic acid, picolinic acid, isonicotinic acid.

Saltene av 1-norefedrin anvendes på samme måte under samme betingelser og i tilsvarende mengder som den fri base av 1-norefedrin. Anvendelsen av saltene er spesielt egnet for ut-førelse av racematspaltningen av D,L-penicillamin når det fore-ligger som N-acetyl- eller fortrinnsvis som N-formyl-derivat, spesielt som N-formyl-2,2,5,5-tetrametyl-tiazolidin-4-karboksylsyre (N-formyl-isopropyliden-D,L-penicillamin) eller N-formyl-2,2-pentametylen-5>5-dimetyl-tiazolidin-4-karboksylsyre. The salts of 1-norephedrine are used in the same way under the same conditions and in similar quantities as the free base of 1-norephedrine. The use of the salts is particularly suitable for carrying out the racemate cleavage of D,L-penicillamine when it is present as N-acetyl or preferably as N-formyl derivative, especially as N-formyl-2,2,5,5 -tetramethyl-thiazolidine-4-carboxylic acid (N-formyl-isopropylidene-D,L-penicillamine) or N-formyl-2,2-pentamethylene-5>5-dimethyl-thiazolidine-4-carboxylic acid.

I det følgende er stoffenes dreieevne angitt som spesifikk dreining /ct/p 20 i grader.cnr/dm.g. Prosentangivelser be-tyr vekt%. In the following, the twistability of the fabrics is indicated as specific twist /ct/p 20 in degrees.cnr/dm.g. Percentages mean % by weight.

Eksempel 1 Example 1

21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin oppløses ved 60 til 70°C i 80 ml n-butylacetat. Opp-løsningen ble under omrøring blandet med 11,7 g (0,06 mol) 1-norefedrin-acetat og deretter holdt 30 minutter ved 80 til 85°C. Det oppsto i første rekke en klar oppløsning; fra denne utskilte det seg noen minutter senere adduktet av N-formyl-isopropyliden-D-penicillamin og 1-norefedrin. ' Etter langsom avkjøling til værelsestemperatur ble det filtrert under avsugning. Det dannede addukt ble vasket med 20 ml n-butylacetat og deretter tør-ket under nedsatt trykk. Det har en spesifikk dreining på + 3^° 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine are dissolved at 60 to 70°C in 80 ml of n-butyl acetate. The solution was mixed with 11.7 g (0.06 mol) of 1-norephedrine acetate with stirring and then kept for 30 minutes at 80 to 85°C. First of all, there was a clear resolution; from this the adduct of N-formyl-isopropylidene-D-penicillamine and 1-norephedrine separated a few minutes later. After slow cooling to room temperature, it was filtered under suction. The adduct formed was washed with 20 ml of n-butyl acetate and then dried under reduced pressure. It has a specific rotation of + 3^°

og et smeltepunkt fra 200 til 203°C. and a melting point from 200 to 203°C.

Utbyttet utgjorde 11,5 g» tilsvarende 63%, referert til anvendt N-formyl-isopropyliden-D,L-penicillamin. The yield was 11.5 g" corresponding to 63%, referred to the N-formyl-isopropylidene-D,L-penicillamine used.

II g av adduktet av N-formyl-isopropyliden-D,L-penicillamin og 1-norefedrin ble suspendert i 40 ml vann. Blan-dingen ble ved værelsestemperatur innstillet med konsentrert salt-syre til pH 1. Iløpet av de følgende 15 minutter utskilte det seg N-formyl-isopropylidin-D-penicillamin. Det ble frafiltrert under frasugning, vasket med 10 ml vann og tørket ved nedsatt trykk. N-formyl-isopropyliden-D-penicillamin hadde en spesi- II g of the adduct of N-formyl-isopropylidene-D,L-penicillamine and 1-norephedrine was suspended in 40 ml of water. The mixture was adjusted at room temperature with concentrated hydrochloric acid to pH 1. During the following 15 minutes, N-formyl-isopropylidine-D-penicillamine separated. It was filtered off with suction, washed with 10 ml of water and dried under reduced pressure. N-formyl-isopropylidene-D-penicillamine had a speci-

fikk dreining på +52° og et smeltepunkt på 182 til 183°C Utbyttet obtained rotation of +52° and a melting point of 182 to 183°C The yield

utgjorde 5»8 g tilsvarende 90%, referert til anvendt addukt. amounted to 5.8 g corresponding to 90%, referred to the adduct used.

Eksempel 2 Example 2

Det ble gått frem som i eks. 1, imidlertid ble It proceeded as in ex. 1, however, was

21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med 21 g (0,1 mol) 1-norefedrin-acetat i 100 ml eddiksyreetyl-ester. Det dannede addukt hadde en spesifikk dreining på +32° 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine reacted with 21 g (0.1 mol) of 1-norephedrine acetate in 100 ml of acetic acid ethyl ester. The adduct formed had a specific rotation of +32°

og et smeltepunkt på 199 til 201°C. Utbyttet utgjorde 15 g, tilsvarende 82%. and a melting point of 199 to 201°C. The yield was 15 g, corresponding to 82%.

Eksempel 3 Example 3

Det ble gått frem som ifølge eksempel 1, imidlertid ble 43,6 g (0,2 mol) N-formyl-isopropyliden-D,L-penicillamin i 180 ml toluen omsatt med 24,8 g (0,11 mol) 1-norefedrinpropionat. Det dannede addukt av N-formyl-isopropyliden-D-penicillamin og 1-norefedrin hadde en spesifikk dreining på +30° og et smeltepunkt fra 201 til 204°C. Utbyttet utgjorde 24 g, tilsvarende 65%. The procedure was as in Example 1, however, 43.6 g (0.2 mol) of N-formyl-isopropylidene-D,L-penicillamine in 180 ml of toluene was reacted with 24.8 g (0.11 mol) of 1- norephedrine propionate. The formed adduct of N-formyl-isopropylidene-D-penicillamine and 1-norephedrine had a specific rotation of +30° and a melting point of 201 to 204°C. The yield was 24 g, corresponding to 65%.

Eksempel 4 Example 4

Det ble gått frem som i eksempel 1, imidlertid ble 21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med 11,5 g (0,02 mol) 1-norefedrin-maleat i 80 ml eddiksyreetyl-ester. Det dannede addukt av N-formyl-isopropyliden-D-penicillamin og 1-norefedrin hadde en spesifikk dreining på +27° og et smeltepunkt fra 199 til 201°C. Utbyttet utgjorde 9,4 g, tilsvarende 51$- The procedure was as in example 1, however, 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine was reacted with 11.5 g (0.02 mol) of 1-norephedrine maleate in 80 ml acetic acid ethyl ester. The formed adduct of N-formyl-isopropylidene-D-penicillamine and 1-norephedrine had a specific rotation of +27° and a melting point from 199 to 201°C. The yield was 9.4 g, corresponding to $51-

Eksempel 5 Example 5

Det ble gått frem som ifølge eksempel 1, imidlertid ble 43,5 g (0,2 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med 30 g (0,11 mol) 1-norefedrin-benzoat. Det dannede addukt hadde en spesifikk dreining på +30° og et smeltepunkt fra 200 til 203°C. Utbyttet utgjorde 24 g, tilsvarende 65%. The procedure was as in Example 1, however, 43.5 g (0.2 mol) of N-formyl-isopropylidene-D,L-penicillamine was reacted with 30 g (0.11 mol) of 1-norephedrine benzoate. The adduct formed had a specific rotation of +30° and a melting point from 200 to 203°C. The yield was 24 g, corresponding to 65%.

Eksempel 6 Example 6

Det ble gått frem som ifølge eksempel 1, imidlertid ble 21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med 10,8 g (0,06 mol) 1-norefedrin-formiat. Det dannede addukt hadde en spesifikk dreining på +32° og et smeltepunkt fra 198 til 201°C. Utbyttet utgjorde 11 g, tilsvarende 60$. The procedure was as in Example 1, however, 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine was reacted with 10.8 g (0.06 mol) of 1-norephedrine formate. The adduct formed had a specific rotation of +32° and a melting point of 198 to 201°C. The yield was 11 g, equivalent to $60.

Eksempel 7 Example 7

Det ble gått frem som ifølge eksempel 1, imidlertid ble 21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med l6,5 g (0,06 mol) 1-norefedrin-3-fenylprpionat. Det dannede addukt hadde en spesifikk dreining på +32° og et smeltepunkt fra 198 til 202°C. Utbyttet utgjorde 11,5 g, tilsvarende 62%. The procedure was as in Example 1, however, 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine was reacted with 16.5 g (0.06 mol) of 1-norephedrine-3- phenylpropionate. The adduct formed had a specific rotation of +32° and a melting point of 198 to 202°C. The yield was 11.5 g, corresponding to 62%.

Eksempel 8 Example 8

Det ble gått frem som i eksempel 1, imidlertid ble 21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med 33 g (0,11 mol) 1-norefedrin-benzensulfonat. Det dannede addukt ..hadde en spesifikk dreining på +31° og et smeltepunkt fra 197 til 199°C. Utbyttet utgjorde 14 g, tilsvarende 76%. The procedure was the same as in Example 1, but 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine were reacted with 33 g (0.11 mol) of 1-norephedrine-benzenesulfonate. The adduct formed ..had a specific rotation of +31° and a melting point of 197 to 199°C. The yield was 14 g, corresponding to 76%.

Eksempel 9 Example 9

Det ble gått frem som i eksempel 1, imidlertid ble 21,7 g (0,1 mol) N-formyl-isopropyliden-D,L-penicillamin omsatt med 21,5 g (0,03 mol) 1-norefedrin-citrat. Det dannede addukt hadde en spesifikk dreining på +30° og et smeltepunkt fra 198 til 200°C. Utbyttet utgjorde 13 g, tilsvarende 70$. The procedure was the same as in Example 1, however, 21.7 g (0.1 mol) of N-formyl-isopropylidene-D,L-penicillamine was reacted with 21.5 g (0.03 mol) of 1-norephedrine citrate. The adduct formed had a specific rotation of +30° and a melting point from 198 to 200°C. The yield was 13 g, equivalent to $70.

Eksempel 10 Example 10

Det ble gått frem som ifølge eksempel 1, imidlertid ble 25,7 g (0,1 mol) D,L-N-formyl-2,2-pentametylen-5,5-dimetyl-tiazolidin-4-karboksylsyre omsatt med 10,8 g (0,06 mol) 1-norefedrin-formiat. Det dannede addukt av D-N-formyl-2,2-pentametylen-5,5-dimetyl-tiazolidin-4-karboksylsyre og 1-norefedrin hadde en spesifikk dreining på +25° og et smeltepunkt fra 190 til 191°C. Utbyttet utgjorde 16,5 g» tilsvarende 815?. Spaltningen av adduktet foregikk som ifølge eksempel 1. Den herved dannede D-N-formyl-2 ,2 -pent ame ty len- 5, 5_dimet yl- tiazolidin-4 -karboksyl syre hadde en spesifikk dreining på +62,8° og et smeltepunkt - fra 190 til 191°C. Utbyttet utgjorde 9,2 g, tilsvarende'905?. The procedure was as in example 1, however, 25.7 g (0.1 mol) of D,L-N-formyl-2,2-pentamethylene-5,5-dimethyl-thiazolidine-4-carboxylic acid was reacted with 10.8 g (0.06 mole) of 1-norephedrine formate. The formed adduct of D-N-formyl-2,2-pentamethylene-5,5-dimethyl-thiazolidine-4-carboxylic acid and 1-norephedrine had a specific rotation of +25° and a melting point of 190 to 191°C. The yield amounted to 16.5 g» corresponding to 815?. The cleavage of the adduct took place as according to example 1. The D-N-formyl-2,2-pentamethylene-5,5-dimethyl-thiazolidine-4-carboxylic acid thus formed had a specific rotation of +62.8° and a melting point - from 190 to 191°C. The yield was 9.2 g, corresponding to '905?.

Eksempel 11 Example 11

Det ble gått frem som ifølge eksempel 1, imidlertid ble 25,7 g (0,1 mol) D,L-N-formyl-2,2-péntametylen-5,5-dimetyl-tiazolidin-4-karboksylsyre omsatt med 16,5 g (0,06 mol) 1-norefedrin-benzensulfonat. Det dannede addukt hadde en spesifikk dreining på +2 4° og et smeltepunkt fra 189 til 191°C Utbyttet utgjorde 14,5 g, tilsvarende 715?. The procedure was as in example 1, however, 25.7 g (0.1 mol) of D,L-N-formyl-2,2-pentamethylene-5,5-dimethyl-thiazolidine-4-carboxylic acid was reacted with 16.5 g (0.06 mole) of 1-norephedrine-benzenesulfonate. The adduct formed had a specific rotation of +2 4° and a melting point from 189 to 191°C. The yield was 14.5 g, corresponding to 715?.

Claims (3)

1. Fremgangsmåte til utvinning av D-penicillamin av D,L-penicillamin ifølge patent nr. 135,9031. Process for the extraction of D-penicillamine from D,L-penicillamine according to patent no. 135,903 karakterisert ved at den anvendte base er 1-norefedrin som anvendes som salt.characterized in that the base used is 1-norephedrine which is used as a salt. 2. Fremgangsmåte ifølge krav 1, karakt e r i -2. Method according to claim 1, character i - s e r t ved at man anvender norefedrin som salt av en sulfonsyre eller karboksylsyre.particularly by using norephedrine as a salt of a sulphonic or carboxylic acid. 3. Fremgangsmåte ifølge krav 2,karakterisert3. Method according to claim 2, characterized ved at man anvender norefedrin som salt av maursyre, eddik-syre eller propionsyre.by using norephedrine as a salt of formic acid, acetic acid or propionic acid.
NO3693/73A 1972-11-29 1973-09-20 PROCEDURE FOR DRAWING D-PENICILLAMINE NO138948C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2258411A DE2258411C3 (en) 1972-11-29 1972-11-29 Process for obtaining D-penicillamine

Publications (2)

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NO138948B true NO138948B (en) 1978-09-04
NO138948C NO138948C (en) 1978-12-13

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NO3693/73A NO138948C (en) 1972-11-29 1973-09-20 PROCEDURE FOR DRAWING D-PENICILLAMINE

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JP (1) JPS5512423B2 (en)
AR (1) AR203731A1 (en)
BE (1) BE806378R (en)
BR (1) BR7309342D0 (en)
CA (1) CA1003853A (en)
CH (1) CH590182A5 (en)
CS (1) CS183693B2 (en)
DD (1) DD109215A6 (en)
DE (1) DE2258411C3 (en)
DK (1) DK146414C (en)
ES (1) ES418693A2 (en)
FI (1) FI56965C (en)
FR (1) FR2207886B2 (en)
GB (1) GB1413038A (en)
HU (1) HU168379B (en)
IE (1) IE38489B1 (en)
IL (1) IL43567A (en)
IT (1) IT1045950B (en)
NL (1) NL163786C (en)
NO (1) NO138948C (en)
RO (1) RO71923A7 (en)
SE (1) SE382048B (en)
SU (1) SU535900A4 (en)
ZA (1) ZA738498B (en)

Also Published As

Publication number Publication date
FI56965B (en) 1980-01-31
AR203731A1 (en) 1975-10-15
JPS4982627A (en) 1974-08-08
FI56965C (en) 1980-05-12
DE2258411B2 (en) 1980-01-24
FR2207886B2 (en) 1978-01-06
GB1413038A (en) 1975-11-05
SE382048B (en) 1976-01-12
CH590182A5 (en) 1977-07-29
IE38489L (en) 1974-05-29
DD109215A6 (en) 1974-10-20
FR2207886A2 (en) 1974-06-21
HU168379B (en) 1976-04-28
BR7309342D0 (en) 1974-08-29
JPS5512423B2 (en) 1980-04-02
AU6244773A (en) 1975-05-15
ES418693A2 (en) 1977-11-01
ZA738498B (en) 1974-10-30
BE806378R (en) 1974-02-15
NO138948C (en) 1978-12-13
DE2258411A1 (en) 1974-06-06
IE38489B1 (en) 1978-03-29
SU535900A4 (en) 1976-11-15
NL163786C (en) 1980-10-15
IL43567A (en) 1976-04-30
DK146414C (en) 1984-03-12
DE2258411C3 (en) 1981-01-22
NL7316344A (en) 1974-05-31
IT1045950B (en) 1980-06-10
CS183693B2 (en) 1978-07-31
RO71923A7 (en) 1981-07-30
NL163786B (en) 1980-05-16
CA1003853A (en) 1977-01-18
DK146414B (en) 1983-10-03

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