Preparation of 6-epi-ampicillin and of 6-epi-α-hydroxybenzylpenicillin

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  • Preparation of 6-epi-ampicillin and of 6-epi-.ALPHA.-hydroxybenzylpenicillin.
  • Preparation of 6 epi ampicillin and of

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The preparation 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 3-7 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 α-hydroxybenzylpenicillin with about 66% of L- and 34% mandelyl side chain. Reaction 6-epi-ampicillin gave 6-epi- α-hydroxybenzylpenicillin with practically the same ratio of L- and D-isomers.

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