3,4-Dichlorophenyl isocyanate → HCID 67151622, compound

Participants

Reaction Steps

To a stirred suspension of (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (180 mg) in dichloromethane (3 ml) were added sequentially N,N-diisopropylethylamine (0.19 ml) and 3,4-dichlorophenyl isocyanate (137 mg, CAS 102-36-3) and stirring was continued at room temperature for 18 h. The mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-(2-{4-[3-(3,4-dichloro-phenyl)-ureido]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (267 mg, 93%) as a colourless amorphous solid. MS (ISP): 529.4 ([{37Cl}M+NH4]+), 527.4 ([{37Cl35Cl}M+NH4]+), 525.4 ([{35Cl}M+NH4]+), 512.2 ([{37Cl}M+H]+), 510.2 ([{37Cl35Cl}M+H]+), 508.2 ([{35Cl}M+H]+), 456.2 ([{37Cl}M+H—C4H8]+), 454.2 ([{37Cl35Cl}M+H—C4H8]+), 452.2 ([{35Cl}M+H—C4H8]+).

Provenance & Evidence