Carbon Tetrachloride → 3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

Participants

Reaction Steps

2.9 g of 3-[3-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyloxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide are dissolved in 45 ml of acetonitrile and 45 ml of carbon tetrachloride and the solution is added to a solution of 8.56 g of sodium periodate and 150 mg of ruthenium(III) chloride hydrate in 85 ml of water. After 5 h, the crude product is isolated by extraction with methylene chloride. The crude product is then dissolved in 200 ml of diethyl ether and the solution is stirred with 10 g of Hyflo® and, after 30 min, filtered over Hyflo®. The filtrate is concentrated and the residue is purified by FC (100 g of silica gel, mobile phase S). The title compound is obtained: Rf (S)=0.35; Rt (II)=11.4 min; FABMS: (M+H)+ =457.

Provenance & Evidence