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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 35, Number 5
JKCSEZ 35(5)
October 20, 1991 

Synthesis of 6-(Carboxymethylthio) penicillanic Acid Derivatives from 6β-Bromopenicillanates

6β-Bromopenicillanate로부터 6-(Carboxymethylthio) penicillanic Acid 유도체의 합성
Won-Sik Choi, Young-Haeng Lee, Chai-Ho Lee

최원식, 이영행, 이채호
6β-bromopenicillanic acid(4a)와 p-nitrobenzylbromide, 3-bromophthalide, chloromethylpivalate 및 1-chlorodiethylcarbonate의 반응으로 6β-bromopenicillanates(4b~4e)을 합성하였으며, 6β-bromopenicillanic acid(4a)와 그의 ester(4b~4e)를 thioglycolic acid와 친핵성 치환반응시켜 새로운 β-lactam계 화합물인 6-(carboxymethylthio)penicillanic acid(5a)와 그의 ester(5b~5e)를 얻었다.

Reaction of 6β-bromopenicillanic acid(4a) with p-nitrobenzylbromide, 3-bromophthalide, chloromethylpivalate and 1-chlorodiethylcarbonate afforded 6β-bromopenicillanates(4b~4e). New β-lactam compound, 6-(carboxymethylthio)penicillanic acid(5a) and the other esters(5b~5e) were prepared by nucleophilic substitution reaction of 6β-bromopenicillanic acid(4a) and the other esters(4b~4e) with thioglycolic acid.

575 - 579
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