GB1347208A - Method of preparing alpha-carboxybenzylpenicillin - Google Patents
Method of preparing alpha-carboxybenzylpenicillinInfo
- Publication number
- GB1347208A GB1347208A GB1912272A GB1912272A GB1347208A GB 1347208 A GB1347208 A GB 1347208A GB 1912272 A GB1912272 A GB 1912272A GB 1912272 A GB1912272 A GB 1912272A GB 1347208 A GB1347208 A GB 1347208A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxybenzylpenicillin
- amide
- formula
- radical
- organic
- 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
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1347208 Preparing α-carboxybenzylpenicillin INSTYTUT PRZEMYSLU FARMACEUTYCNEGO 25 April 1972 [5 May 1971] 19122/72 Heading C2A α-Carboxybenzylpenicillin and salts thereof, having the Formula (1): in which X is hydrogen or the cation of an alkali metal or alkaline earth metal, are prepared by condensing 6-aminopenicillanic acid (6-APA) or a salt thereof with an acylating derivative of an N-substituted or unsubstituted monoamide of phenylmalonic acid, said acid having the Formula (2): wherein R 1 and R 2 each represents hydrogen, a straight or branched aliphatic radical (preferably having 1 to 4 carbons), a cycloaliphatic radical, a substituted or unsubstituted aryl radical or an alkylaryl radical, and R 1 and R 2 may be identical or different; to give an amide of α- carboxybenzylpenicillin of Formula (3): wherein R 1 , R 2 and X have the aforesaid meanings; and then hydrolysing the said amide (3) to give the desired compound (1). The preferred acylating derivative of the compound (2) is its mixed anhydride with an alkyl (e.g. ethyl) chloroformate. The condensation with 6-APA is carried out in organic or organic-aqueous (e.g. acetone/water) medium containing sodium bicarbonate. The amide (3) may be hydrolysed directly in the reaction mixture, preferably after evaporation of the organic solvent, or may be first isolated and re-crystallized. The hydrolysis step is effected in aqueous solution at a pH below 8À5, if required with warming, e.g. to about 35‹ C., using a saturated solution of borax, sodium bicarbonate or disodium phosphate. The product (1) is then isolated by acidifying the solution, extracting the product with ether and precipitating as the Na salt by adding ethereal sodium ethylcapronate. Reference has been directed by the Comptroller to Specification 1,004,670.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL14795871A PL76934B1 (en) | 1971-05-05 | 1971-05-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1347208A true GB1347208A (en) | 1974-02-27 |
Family
ID=19954271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1912272A Expired GB1347208A (en) | 1971-05-05 | 1972-04-25 | Method of preparing alpha-carboxybenzylpenicillin |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS5243838B1 (en) |
CS (1) | CS186762B2 (en) |
DD (1) | DD97657A5 (en) |
GB (1) | GB1347208A (en) |
HU (1) | HU164262B (en) |
PL (1) | PL76934B1 (en) |
SE (1) | SE385373B (en) |
SU (1) | SU452100A3 (en) |
-
1971
- 1971-05-05 PL PL14795871A patent/PL76934B1/xx unknown
-
1972
- 1972-04-25 GB GB1912272A patent/GB1347208A/en not_active Expired
- 1972-05-03 DD DD16271672A patent/DD97657A5/xx unknown
- 1972-05-04 SE SE589072A patent/SE385373B/en unknown
- 1972-05-04 JP JP4376672A patent/JPS5243838B1/ja active Pending
- 1972-05-04 SU SU1781077A patent/SU452100A3/en active
- 1972-05-04 CS CS303072A patent/CS186762B2/en unknown
- 1972-05-05 HU HUII000095 patent/HU164262B/hu unknown
Also Published As
Publication number | Publication date |
---|---|
DD97657A5 (en) | 1973-05-12 |
HU164262B (en) | 1974-01-28 |
CS186762B2 (en) | 1978-12-29 |
PL76934B1 (en) | 1975-02-28 |
JPS5243838B1 (en) | 1977-11-02 |
SU452100A3 (en) | 1974-11-30 |
SE385373B (en) | 1976-06-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed |