Process for preparing 7-aminocephalosporanic acid derivatives

Details Process for preparing 7-aminocephalosporanic acid derivatives Process for preparing 7-aminocephalosporanic acid derivatives

1976-01-20

1978-03-14

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

544 30, C07D50104

Patent

active

040791807

ABSTRACT:
7-Aminocephalosporanic acid derivatives represented by the general formula (III), ##STR1## wherein X is hydrogen, hydroxyl, acetate or a nucleophilic residue, which are useful as a starting material for the synthesis of cephalosporin type antibiotics low in toxicity and broad in pharmacological effect can be easily prepared by allowing to react cephalosporin C or its derivative represented by the general formula (I), ##STR2## wherein X is as defined above, or a salt thereof with an .alpha.-keto derivative represented by the general formula (II), ##STR3## wherein R.sub.1 is carboxyl, aroyl or amide when R.sub.2 is hydrogen, and is carboxyl when R.sub.2 is alkyl or aryl, or its salt. In this case, the yield of the 7-aminocephalosporanic acid derivatives can be remarkably improved by carrying out the reaction in the presence of hydrogen peroxide. The yield can be further improved by adding thiosulfuric acid or a salt thereof after the completion of the reaction to decompose the unreacted hydrogen peroxide.

REFERENCES:
patent: 3928324 (1975-12-01), Rosati
patent: 3932392 (1976-01-01), Johnson et al.
patent: 3962223 (1976-06-01), Martel et al.

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