Pyridine → HCID 70508183, compound

Participants

Reaction Conditions

Reaction Steps

By the procedure of Example 18, pivaloyloxymethyl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate (135 mg., 0.3 mmoles) was reduced with tetrabutylammonium borohydride and the isolation taken to the stage at which a washed, dried and filtered solution of pivaloyloxymethyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate in methylene chloride was in hand. This solution was cooled to -10° C. Pyridine (24 mg., 0.3 mmoles), acetic anhydride (31 mg., 0.3 mmoles) and 4-dimethylaminopyridine (4 mg., 0.3 mmoles) were added in sequence. After stirring for 1 hour at -10° C., tlc (4:1 chlorform:ethyl acetate) indicated complete acetylation. The reaction mixture was diluted with toluene and stripped to dryness in vacuo, with toluene chases. Chromatography on silica gel (20:1 methylene chloride:ethyl acetate) gave pivaloyloxymethyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [10 mg.; Rf 0.36 (4:1 chloroform:ethyl acetate); ir (CH2Cl2) 1780, 1750, 1685 cm- ].

Provenance & Evidence