GB716337A - Manufacture of pantetheine - Google Patents
Manufacture of pantetheineInfo
- Publication number
- GB716337A GB716337A GB3003851A GB3003851A GB716337A GB 716337 A GB716337 A GB 716337A GB 3003851 A GB3003851 A GB 3003851A GB 3003851 A GB3003851 A GB 3003851A GB 716337 A GB716337 A GB 716337A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alanine
- aralkylthioethylamine
- carboaralkoxy
- alanyl
- carbo
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- ZNXZGRMVNNHPCA-UHFFFAOYSA-N Pantetheine Natural products OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-UHFFFAOYSA-N 0.000 title abstract 3
- ZNXZGRMVNNHPCA-VIFPVBQESA-N pantetheine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-VIFPVBQESA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000008064 anhydrides Chemical class 0.000 abstract 4
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 2
- 229960003151 mercaptamine Drugs 0.000 abstract 2
- SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-UHFFFAOYSA-N 0.000 abstract 2
- 229940115458 pantolactone Drugs 0.000 abstract 2
- SIEVQTNTRMBCHO-UHFFFAOYSA-N pantolactone Natural products CC1(C)OC(=O)CC1O SIEVQTNTRMBCHO-UHFFFAOYSA-N 0.000 abstract 2
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Abstract
Pantetheine is obtained by reacting a mixed anhydride of carbo-aralkoxy-b -alanine or an alkyl ester of carbo-aralkoxy-b -alanine with an aralkylthioethylamine, e.g. 2-benzylthioethylamine in the presence of an inert solvent to produce N - (carbo - aralkoxy - b - alanyl) - 2 - aralkylthioethylamine, removing the aralkyl and carbo-aralkoxy groups from the N-(carboaralkoxy - b - alanyl) - 2 - aralkylthioethylamine by hydrogenolysis and reacting the resulting amino-thiol, N-b -alanyl-2-mercaptoethylamine, with pantolactone to produce pantetheine. The aralkylthioethylamine is reacted with the mixed anhydride of carboaralkoxy-b -alanine in the temperature range 0 DEG to 20 DEG C. and with the alkyl ester of carboaralkoxy-b -alanine in the temperature range 50 DEG to 150 DEG C. As mixed anhydride of carboaralkoxy-b -alanine there may be used an azide, chloride of sulphuric anhydride. The hydrogenolysis may be effected with alkali metal, e.g. sodium and liquid ammonia. The N-b -alanyl-2-mercaptoethylamine is reacted with pantolactone at approximately 100 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3003851A GB716337A (en) | 1951-12-21 | 1951-12-21 | Manufacture of pantetheine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3003851A GB716337A (en) | 1951-12-21 | 1951-12-21 | Manufacture of pantetheine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB716337A true GB716337A (en) | 1954-10-06 |
Family
ID=10301271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3003851A Expired GB716337A (en) | 1951-12-21 | 1951-12-21 | Manufacture of pantetheine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB716337A (en) |
-
1951
- 1951-12-21 GB GB3003851A patent/GB716337A/en not_active Expired
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