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

Participants

Reaction Steps

A solution of 809 mg of pyridinium dichromate in 2 ml of N,N-dimethylformamide is added dropwise via a cannula to a solution of 290 mg of 3-[N-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide in 2 ml of N,N-dimethylformamide at room temperature under argon. After 23 h, a further 238 mg of pyridinium dichromate are added. After a total of 29 h, the reaction mixture is poured into water, extracted with diethyl ether (3 times), dried (Na2SO4) and concentrated. Purification over silica gel (mobile phase P) gives the title compound: Rf (P)=0.48; FAB-MS: (M+H)+ =497.

Provenance & Evidence