Preparation of 6-epi-ampicillin and of 6-epi-.ALPHA.-hydroxybenzylpenicillin.
- 1 January 1977
- journal article
- research article
- Published by Japan Antibiotics Research Association in The Journal of Antibiotics
- Vol. 30 (10) , 847-855
- https://doi.org/10.7164/antibiotics.30.847
Abstract
The preparation 6-epi-ampicillin by hydrolysis of 6-epihetacillin is described. During this conversion, formation of a diketopiperazine was observed. The best yield was obtained at pH 7.0 and room temperature for 3-7 h. The lowest yield of 6-epi-ampicillin and highest formation of the diketopiperazine occurred in pyridine-acetic acid-water. Treatment of ampicillin (with D-aminophenylacetyl side chain) with nitrous acid gave .alpha.-hydroxybenzylpenicillin with about 66% of L- and 34% mandelyl side chain. Reaction 6-epi-ampicillin gave 6-epi-.alpha.-hydroxybenzylpenicillin with practically the same ratio of L-and D-isomers.This publication has 1 reference indexed in Scilit:
- EpihetacillinTetrahedron Letters, 1968