Fluoride Ion → 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

Participants

Reaction Steps

474 mg of 3-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide are dissolved in 5 ml of tetrahydrofuran, and 1.2 ml of a 1M tetraburylammonium fluoride solution in tetrahydrofuran are added at room temperature under argon. After 4 h, the reaction mixture is diluted with diethyl ether, washed with water and brine, dried (Na2SO4) and concentrated. Purification over silica gel (mobile phase A) gives the title compound: Rf (A)=0.40; FAB-MS: (M+H)+ =483.

Provenance & Evidence