Acetic Acid → HCID 131712810, compound

Participants

Reaction Conditions

Reaction Steps

Pivaloyloxymethyl 2-diazo-3-methyl-1-betaoxoceph-3-em-4-carboxylate (150 mg., 0.42 mmoles) was converted to a methylene chloride solution of pivaloyloxymethyl 2-methyl-1-oxocarbapen-2-em-3-carboxylate by the method of Example 1. Without isolation, and while continuing to maintain the temperature at -78° C., tetrabutylammonium borohydride (26.4 mg., 0.092 mmole) was added and the mixture stirred for 30 minutes. The reaction was quenched with acetic acid (0.58 equivalent), extracted twice with aqueous buffer (pH 7), dried over anhydrous sodium sulfate and filtered to yield a methylene chloride solution of pivaloyloxymethyl 1-hydroxy-2-methylcarbapen-2-em-3-carboxylate [ir (CH2Cl2) 1780, 1745 cm-1 ; Rf 0.25, (4:1 chloroform:ethyl acetate)]. If desired, this product is further isolated by evaporation in vacuo, keeping the temperature as low as possible to minimize degradation.

Provenance & Evidence