Title: Preparation of 6-epi-ampicillin and of 6-epi-alpha-hydroxybenzylpenicillin
Authors: Roets, Eugene ×
Vlietinck, A
Vanderhaeghe, Hubert #
Issue Date: Oct-1977
Publisher: Japan antibiot res assn
Series Title: The Journal of antibiotics vol:30 issue:10 pages:847-55
Abstract: The preparation of 6-epi-ampicillin by hydrolysis of 6-epihetacillin is described. During this conversion, the formation of a diketopiperazine was also observed. The best yield was obtained at pH 7.0 and room temperature for 3 approximately 7 hours. The lowest yield of 6-epi-ampicillin and the 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.
ISSN: 0021-8820
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Pharmaceutical Analysis
Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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