4-Chloroaniline → HCID 67151580, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of (RS)-4-(4-carboxy-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (80 mg) in THF (4 ml) were added sequentially N-methylmorpholine (0.11 ml), TBTU (160 mg) and 4-chloro-aniline (48 mg) and the mixture was heated at 50° C. for 18 h. The mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-[4-(4-chloro-phenylcarbamoyl)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (110 mg, quant.) as a light yellow solid. MS (ISP): 455.2 ([{37Cl}M+Na]+), 453.2 ([{35Cl}M+Na]+), 433.3 ([{37Cl}M+H]+), 431.4 ([{35Cl}M+H]+), 377.3 ([{37Cl}M+H—C4H8]+), 375.3 ([{35Cl}M+H—C4H8]+).

Provenance & Evidence