GB1311268A - Process for the isolation of n-benzoyl cephalosporin c - Google Patents

Process for the isolation of n-benzoyl cephalosporin c

Info

Publication number
GB1311268A
GB1311268A GB2711871A GB2711871A GB1311268A GB 1311268 A GB1311268 A GB 1311268A GB 2711871 A GB2711871 A GB 2711871A GB 2711871 A GB2711871 A GB 2711871A GB 1311268 A GB1311268 A GB 1311268A
Authority
GB
United Kingdom
Prior art keywords
cephalosporin
benzoyl
imino
derivative
alcohol
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
Application number
GB2711871A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Inc
Original Assignee
Pfizer Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of GB1311268A publication Critical patent/GB1311268A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D501/00Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02Preparation
    • C07D501/12Separation; Purification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1311268 N-Benzoyl-cephalosporin C PFIZER Inc 19 April 1971 [26 Jan 1971] 27118/71 Heading C2A Cephalosporin C is recovered from a cephalosporin C-containing fermentation broth by treating the broth with benzoyl chloride at a pH of 7 to 10 and a temperature of 10 to 15‹ C. to form the N-benzoyl derivative of cephalosporin C, and then acidifying to pH 1 to 3 and extracting the derivative by means of a waterimmiscible solvent. The derivative may then be cleaved to 7-aminocephalosporanic acid, e.g. by conversion to the silyl ester with chlorotrimethylsilane, halogenating the ester with PCl 5 in anhydrous pyridine to form the imino-halide, converting the latter to the imino-ether by treatment with an alcohol and then hydrolysing or alcoholysing the imino-ether to give 7-aminocephalosporanic acid. The fermentation broth may be subjected to a preliminary treatment with 50% sulphuric acid to bring the pH to 2À5 followed by standing at 5‹ C. to room temperature to destroy co-produced penicillin N. Suitable water-immiscible extracting solvents are alcohols (e.g. n-butanol, n-amyl alcohol, n-hexanol or benzyl alcohol), esters, water-immiscible ketones and chlorinated hydrocarbons. The extract is purified with charcoal, concentrated and taken up in acetone. The acetone solution is treated with sodium ethyl hexanoate to precipitate the crystalline monosodium salt of N-benzoyl cephalosporin C, from which free N-benzoyl cephalosporin C is obtained by acidification with sulphuric acid. Reference has been directed by the Comptroller to Specification 847,375.
GB2711871A 1971-01-26 1971-04-19 Process for the isolation of n-benzoyl cephalosporin c Expired GB1311268A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10993371A 1971-01-26 1971-01-26

Publications (1)

Publication Number Publication Date
GB1311268A true GB1311268A (en) 1973-03-28

Family

ID=22330355

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2711871A Expired GB1311268A (en) 1971-01-26 1971-04-19 Process for the isolation of n-benzoyl cephalosporin c

Country Status (4)

Country Link
JP (1) JPS5417832B1 (en)
DE (1) DE2157693C3 (en)
FR (1) FR2114935A5 (en)
GB (1) GB1311268A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1015745A (en) * 1972-06-27 1977-08-16 Fujisawa Pharmaceutical Co. 3-substituted-methyl-3-cephem-4-carboxylic acid derivatives and preparation thereof
SU603343A3 (en) * 1972-11-13 1978-04-15 Эли Лилли Энд Компани (Фирма) Method of purifying c cephalosporin
FR2404642A1 (en) * 1977-09-29 1979-04-27 Roussel Uclaf NEW DERIVATIVE OF CEPHALOSPORIN C, PROCESS FOR PREPARATION AND APPLICATION OF THE NEW PRODUCT TO THE PREPARATION OF 7-AMINO CEPHALOSPORANIC ACID

Also Published As

Publication number Publication date
FR2114935A5 (en) 1972-06-30
DE2157693C3 (en) 1980-09-11
JPS5417832B1 (en) 1979-07-03
DE2157693A1 (en) 1972-09-21
DE2157693B2 (en) 1980-01-17

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee