Synthesis of α‐hydroxy‐β‐lactams

M. S. Marthas, S. G. Amin, H. P.S. Chawk, Ajay K. Bose

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A convenient synthesis of α‐hydroxy‐β‐lactams has been devised that involves the annelation of an inline with benzyloxyacetyl chloride and triethylamine and subsequent hydrogenolysis in the presence of palladium on carbon. In most cases a cis‐β‐lactam was obtained. A thioimidate can also be used as the imino component in the annelation reaction but the hydrogenolysis step fails. The annelation of the appropriate thiazoline to a 6‐epi‐penicillin derivative occurred much more readily with benzyloxyacetyl chloride than with azidoacetyl chloride.

Original languageEnglish (US)
Pages (from-to)601-604
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume15
Issue number4
DOIs
StatePublished - Jun 1978

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Chlorides
Hydrogenolysis
Palladium
Carbon
Derivatives
triethylamine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Marthas, M. S. ; Amin, S. G. ; Chawk, H. P.S. ; Bose, Ajay K. / Synthesis of α‐hydroxy‐β‐lactams. In: Journal of Heterocyclic Chemistry. 1978 ; Vol. 15, No. 4. pp. 601-604.
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Synthesis of α‐hydroxy‐β‐lactams. / Marthas, M. S.; Amin, S. G.; Chawk, H. P.S.; Bose, Ajay K.

In: Journal of Heterocyclic Chemistry, Vol. 15, No. 4, 06.1978, p. 601-604.

Research output: Contribution to journalArticle

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