Potassium Carbonate → (3S-trans)-2-[[3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-2-oxo-1-azetidinyl]oxy]-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester

Participants

Reaction Steps

To a solution of (3S-trans)-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methyl-1-hydroxy-2azetidinone (55 mg, 0.26 mmol) and (S)-2-bromo-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester (110 mg, 0.26 mmol) in dimethylformamide (1 ml) was added potassium carbonate (100 mg, 1 mmol). The resulting slurry was stirred for three hours at room temperature, quenched with hydrochloric acid (1N, 10 ml) and extracted with ether (20 ml). The organic layer was washed twice with dilute hydrochloric acid (1N, 2×10 ml), with saturated sodium chloride solution (20 ml), dried over magnesium sulfate and evaporated at reduced pressure. Purification of the product by preparative thin layer chromatography afforded the title compound (108 mg) as a mixture of diastereomers.

Provenance & Evidence