4-Chlorobenzyl alcohol → HCID 67151716, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of (S)-4-[2-(4-isocyanato-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (240 mg) in 1,2-dichloroethane (2 ml) in a pressure tube were added sequentially N,N-diisopropylethylamine (0.24 ml) and 4-chloro-benzyl alcohol (148 mg). The tube was capped and stirring was continued while the reaction mixture was heated at 110° C. for 18 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-{2-[4-(4-chloro-benzyloxycarbonylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (174 mg, 51%) as a colourless amorphous solid. MS (ISP): 508.2 ([{37Cl}M+NH4]+), 506.2 ([{35Cl}M+NH4]+), 491.2 ([{37Cl}M+H]+), 489.2 ([{35Cl}M+H]+), 435.2 ([{37Cl}M+H—C4H8]+), 433.2 ([{35Cl}M+H—C4H8]+).

Provenance & Evidence