GB591435A - Manufacture of n-acetyl-penicillamine and 2:5:5-trimethyl-thiazoline-4-carboxylic acid - Google Patents
Manufacture of n-acetyl-penicillamine and 2:5:5-trimethyl-thiazoline-4-carboxylic acidInfo
- Publication number
- GB591435A GB591435A GB1170145A GB1170145A GB591435A GB 591435 A GB591435 A GB 591435A GB 1170145 A GB1170145 A GB 1170145A GB 1170145 A GB1170145 A GB 1170145A GB 591435 A GB591435 A GB 591435A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillamine
- acetyl
- carboxylic acid
- thiazoline
- trimethyl
- 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
- MNNBCKASUFBXCO-YFKPBYRVSA-N N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)S MNNBCKASUFBXCO-YFKPBYRVSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- APWYYAGSRXGLQQ-UHFFFAOYSA-N 2-methyl-4-propan-2-ylidene-1,3-oxazol-5-one Chemical compound CC(C)=C1N=C(C)OC1=O APWYYAGSRXGLQQ-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 Acetic Acid Drugs 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing Effects 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000003495 polar organic solvent 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
N-acetyl-penicillamine is obtained by hydrolysing 2 : 5 : 5-trimethylthiazoline-4-carboxylic acid produced by the interaction of hydrogen sulphide with 2-methyl-4-isopropylidene-oxazol-5-one in the presence of a polar organic solvent, e.g. methyl alcohol, ethyl alcohol, glacial acetic acid and ethyl acetate. In an example using the reagents above, hydrolysis is effected by heating with water.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB591435A true GB591435A (en) | 1947-08-18 |
Family
ID=1711366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1170145A Expired GB591435A (en) | 1945-05-10 | Manufacture of n-acetyl-penicillamine and 2:5:5-trimethyl-thiazoline-4-carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB591435A (en) |
-
1945
- 1945-05-10 GB GB1170145A patent/GB591435A/en not_active Expired
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