Benzoic Acid → HCID 57068111, compound

Participants

Reaction Steps

In 2 ml of tetrahydrofuran were dissolved (3S, 4R)-3-[(S)-1-hydroxyethyl]-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2-one (105 mg, 0.38 mmole), triphenylphosphine (201 mg, 2 equivalents) and benzoic acid (94 mg, 2 equivalents). To the resulting solution was added little by little a solution of diethyl azodicarboxylate (134 mg, 2 equivalents) in tetrahydrofuran (1 ml) at 20° C. over 10 minutes and then the mixture was stirred at the same temperature for 1.5 hours. The solvent was then distilled off and the residue was dissolved in 3 ml of a 6:1 by volume mixture of benzene and ethyl acetate and left to stand in a refrigerator. The resulting precipitate was filtered off and the filtrate was subjected to thin layer chromatography developed with a 5:1 by volume mixture of benzene and ethyl acetate to afford 119 mg (yield 82%) of the desired product as an oil, containing a small amount of the 1'S-isomer.

Provenance & Evidence