Phosphorus in organic synthesis. XII. Amino acids and peptides. XXII. Reaction of penicillin sulfoxides with diethyl phosphorocyanidate (DEPC).
- 1 January 1976
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 24 (11) , 2711-2715
- https://doi.org/10.1248/cpb.24.2711
Abstract
Reaction of penicillin sulfoxides with diethyl phosphorocyanidate (DEPC) was investigated. Treatment of a benzylpenicillin (S)-sulfoxide methyl ester with a slight excess of DEPC in N,N-dimethylacetamide gave a 3-cephem, a 2-cephem and a 3-methylenecepham in 22, 4 and 4% yields, respectively. Increase of the quantity of DEPC to a 3- or 5-fold excess increased the yield of the 3-cephem. Phenoxymethylpenicillin (S)-sulfoxide methyl ester also afforded a 3-cephem and a 3-methylenecepham under analogous reaction conditions as above, while phthalimidopenicillin (R)-sulfoxide methyl ester furnished a 3-cephem and 2 isothiazolones.This publication has 1 reference indexed in Scilit:
- Phosphorus in organic synthesis—XI Amino acids and peptides—XXITetrahedron, 1976