GB596547A - Improvements in and relating to the preparation of optically active esters of isopropylidenepenicillamine and of penicillamine - Google Patents
Improvements in and relating to the preparation of optically active esters of isopropylidenepenicillamine and of penicillamineInfo
- Publication number
- GB596547A GB596547A GB1946045A GB1946045A GB596547A GB 596547 A GB596547 A GB 596547A GB 1946045 A GB1946045 A GB 1946045A GB 1946045 A GB1946045 A GB 1946045A GB 596547 A GB596547 A GB 596547A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillamine
- hydrogen chloride
- optically active
- isopropylidenepenicillamine
- treatment
- 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
- 229960001639 penicillamine Drugs 0.000 title abstract 3
- VVNCNSJFMMFHPL-VKHMYHEASA-N Penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- -1 penicillamine ester Chemical class 0.000 abstract 2
- LWJROJCJINYWOX-UHFFFAOYSA-L Mercury(II) chloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 abstract 1
- 229940049954 Penicillin Drugs 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 230000001476 alcoholic Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229960000626 benzylpenicillin Drugs 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960002523 mercuric chloride Drugs 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Optically active isopropylidenepenicillamine esters are produced by the hydrolysis and esterification of N-formylisopropylidene penicillamine simultaneously by the action of anhydrous hydrogen chloride in an anhydrous alcohol or successively by treating with a diazohydrocarbon, e.g. diazomethane, and the corresponding alcoholic hydrogen chloride, e.g. hydrogen chloride in methyl alcohol. The dextro compounds are of interest in the preparation of penicillin - like substances. a - Isopropylidine - penicillamine methyl ester is obtained in examples by (1) treatment with dry hydrogen chloride in anhydrous methyl alcohol; (2) esterification with diazomethane followed by hydrolysis with dry hydrogen chloride in dry methyl alcohol. The optically active penicillamine ester is obtained from the ester hydrochloride produced in example (1) above by treatment with mercuric chloride or alternatively by boiling with water and treatment with alkali. Specifications 585,250 and 585,413 are referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB596547A true GB596547A (en) | 1948-01-06 |
Family
ID=1734754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1946045A Expired GB596547A (en) | 1945-07-30 | Improvements in and relating to the preparation of optically active esters of isopropylidenepenicillamine and of penicillamine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB596547A (en) |
-
1945
- 1945-07-30 GB GB1946045A patent/GB596547A/en not_active Expired
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