GB585436A - Improvements in and relating to the production of dl-n-formyl-isopropylidene-penicillamine - Google Patents
Improvements in and relating to the production of dl-n-formyl-isopropylidene-penicillamineInfo
- Publication number
- GB585436A GB585436A GB2220444A GB2220444A GB585436A GB 585436 A GB585436 A GB 585436A GB 2220444 A GB2220444 A GB 2220444A GB 2220444 A GB2220444 A GB 2220444A GB 585436 A GB585436 A GB 585436A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formyl
- isopropylidenepenicillamine
- acetic anhydride
- isolate
- benzene
- 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
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
d - N - Formyl - isopropylidenepenicillamine is obtained via the racemization of the corresponding l-compound by heating the latter above 60 DEG C. with a suitable acylating or halogenating agent. Specified substances are acetic anhydride, propionic anhydride and acetyl chloride, thionyl chloride and phosphorus trichloride; hot anhydrous formic acid is applicable, but disadvantageous. An inert diluent of boiling-point exceeding 60 DEG C. may optionally be present. The racemic product is hydrolysed to penicillamine hydrochloride by warming with 2N-hydrochloric acid, which, in turn, is converted into isopropylidenepenicillamine hydrochloride by warming with acetone, this compound being resolved by the methods described in Specification 585,413 to obtain the requisite d-isomer. In examples: l-N-formyl-isopropylidenepenicillamine is heated with (1) acetic anhydride; (2) acetyl chloride; (3) 98 per cent formic acid and the respective solutions are concentrated in vacuo to isolate dl-N-formyl-isopropylidenepenicillamine; (4) l-N-formyl - isopropylidenepenicillamine is boiled with 98 per cent formic acid for 15 hours to isolate the racemic product; l-N-formyl-isopropylidenepenicillamine is heated on the steam-bath with (5) benzene and phosphorus trichloride; (6) benzene and thionyl chloride; (7) benzene and acetic anhydride; and (8) light petroleum and acetic anhydride, to isolate the racemic product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2220444A GB585436A (en) | 1944-11-10 | 1944-11-10 | Improvements in and relating to the production of dl-n-formyl-isopropylidene-penicillamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2220444A GB585436A (en) | 1944-11-10 | 1944-11-10 | Improvements in and relating to the production of dl-n-formyl-isopropylidene-penicillamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB585436A true GB585436A (en) | 1947-02-06 |
Family
ID=10175609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2220444A Expired GB585436A (en) | 1944-11-10 | 1944-11-10 | Improvements in and relating to the production of dl-n-formyl-isopropylidene-penicillamine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB585436A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112500323A (en) * | 2020-12-17 | 2021-03-16 | 成都大学 | Preparation method of L-penicillamine |
-
1944
- 1944-11-10 GB GB2220444A patent/GB585436A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112500323A (en) * | 2020-12-17 | 2021-03-16 | 成都大学 | Preparation method of L-penicillamine |
| CN112500323B (en) * | 2020-12-17 | 2022-08-19 | 成都大学 | Preparation method of L-penicillamine |
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