GB585413A - Improved method for the resolution of penicillamine - Google Patents
Improved method for the resolution of penicillamineInfo
- Publication number
- GB585413A GB585413A GB1165544A GB1165544A GB585413A GB 585413 A GB585413 A GB 585413A GB 1165544 A GB1165544 A GB 1165544A GB 1165544 A GB1165544 A GB 1165544A GB 585413 A GB585413 A GB 585413A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillamine
- hydrochloride
- formylisopropylidenepenicillamine
- isolated
- aqueous
- 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
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
dl-Penicillamine is resolved into the d- and l-optical isomers by combining its racimic N-formyl - isopropylidene derivative with an optically-active alkaloid, fractionally crystallising the resulting salts from aqueous or alcoholic solution and hydrolysing at least one such isomer, e.g. by warming with aqueous hydrochloric acid. In examples: (1) dl-N-formylisopropylidenepenicillamine is dissolved with brucine in hot water and crystallised, the filtrate being further concentrated, and the combined solids, on treatment in aqueous suspension with concentrated hydrochloric acid, dissolved to yield d-N-formyl-isopropylidenepenicillamine, the corresponding l-compound being isolated from the aqueous filtrate from the resolution on treatment with concentrated hydrochloric acid; d - penicillamine hydrochloride is obtained from the d-N-formyl compound by heating the latter on a steam-bath with 2N-hydrochloric acid in the presence of carbon dioxide, and the free amine is isolated by heating the foregoing hydrochloride with dry acetone for 1 hour and concentrating in vacuo to obtain d-isopropylidenepenicillamine hydrochloride, which is hydrolysed to the corresponding free base by treating with aqueous pyridine, from which d-penicillamine is isolated; (2) dl-N-formylisopropylidenepenicillamine and d-q -ephidrine are dissolved together in water and concentrated to obtain the corresponding l- and d-isomers from the solid and filtrate respectively, d-penicillamine hydrochloride being obtained as in (1); (3) dl-N-formylisopropylidenepenicillamine and l-ephidrine are dissolved together in alcohol, the crude l-isomer being obtained on acidifying the first, and the crude d-isomer on acidifying the second crop of crystals, from which latter d-penicillamine hydrochloride is isolated as in (1); (4) dl-N-formylisopropylidenepenicillamine and l-ephedrine are dissolved together in water to furnish the l-ephedrine salt of l-N-formylisopropylidenepenicillamine and the corresponding l-base is obtained on acidifying, the crude d-isomer being isolated from the filtrate, from which d-penicillamine hydrochloride is obtained as in (1). Specification 585,439 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1165544A GB585413A (en) | 1944-06-19 | 1944-06-19 | Improved method for the resolution of penicillamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1165544A GB585413A (en) | 1944-06-19 | 1944-06-19 | Improved method for the resolution of penicillamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB585413A true GB585413A (en) | 1947-02-06 |
Family
ID=9990241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1165544A Expired GB585413A (en) | 1944-06-19 | 1944-06-19 | Improved method for the resolution of penicillamine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB585413A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2214814A1 (en) * | 1972-03-25 | 1973-09-27 | Degussa | Synthetic d-penicillamine prepns - useful against fibrosis polyarthritis aggressive hepatitis etc |
| US4847297A (en) * | 1985-06-08 | 1989-07-11 | Degussa Aktiengesellschaft | Use of penicillamine for treating immune damaging illnesses |
| CN112500323A (en) * | 2020-12-17 | 2021-03-16 | 成都大学 | Preparation method of L-penicillamine |
-
1944
- 1944-06-19 GB GB1165544A patent/GB585413A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2214814A1 (en) * | 1972-03-25 | 1973-09-27 | Degussa | Synthetic d-penicillamine prepns - useful against fibrosis polyarthritis aggressive hepatitis etc |
| US4847297A (en) * | 1985-06-08 | 1989-07-11 | Degussa Aktiengesellschaft | Use of penicillamine for treating immune damaging illnesses |
| 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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