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[Studies on the synthetic methods of 4-unsubstituted monocyclic beta-lactam antibiotics].

Qing Dong, Liu Df

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Abstract

The key intermediate of monocyclic beta-lactams, N-benzyloxycarbonyl-3 S-amino-2-oxoazetidine(Ⅲ),was synthesized from L-( + )-2,3-diaminopropanoie acid(Ⅰ) by Ph_3P—(PyS)_2—CH_3CN system and N-benzyloxycarbonylation. Ⅰ was prepared from L(+)-aspartic acid by Schmidt rearrangement.Three derivatives(Ⅷa~c) of this monocyclic beta-lactam were prepared and their biological activities evaluated.

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What this paper is about

The key intermediate of monocyclic beta-lactams, N-benzyloxycarbonyl-3 S-amino-2-oxoazetidine(Ⅲ),was synthesized from L-( + )-2,3-diaminopropanoie acid(Ⅰ) by Ph_3P—(PyS)_2—CH_3CN system and N-benzyloxycarbonylation. Ⅰ was prepared from L(+)-aspartic acid by Schmidt rearrangement.Three derivatives(Ⅷa~c) of this monocyclic beta-lactam were prepared and their biological activities evaluated.

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Available abstract

The key intermediate of monocyclic beta-lactams, N-benzyloxycarbonyl-3 S-amino-2-oxoazetidine(Ⅲ),was synthesized from L-( + )-2,3-diaminopropanoie acid(Ⅰ) by Ph_3P—(PyS)_2—CH_3CN system and N-benzyloxycarbonylation. Ⅰ was prepared from L(+)-aspartic acid by Schmidt rearrangement.Three derivatives(Ⅷa~c) of this monocyclic beta-lactam were prepared and their biological activities evaluated.

Key concepts: Lactam, Beta-lactam, Chemistry, Antibiotics, Aspartic acid, Stereochemistry, BETA (programming language), Organic chemistry

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