4-Chlorobenzamide → (RS)-4-[4-(4-chloro-benzoylamino)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (400 mg, Example 1e), 4-chlorobenzamide (185 mg), copper(I) iodide (20 mg), N,N′-dimethylglycine (20 mg) and potassium phosphate (1.05 g) in DMSO (2 ml) in a sealed tube was heated at 110° C. overnight. The mixture was then cooled to room temperature and was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-[4-(4-chloro-benzoylamino)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (297 mg, 69%) as a white solid. MS (ISP): 450.2 ([{37Cl}M+NH4]+), 448.2 ([{35Cl}M+NH4]+), 433.2 ([{37Cl}M+H]+), 431.2 ([{35Cl}M+H]+), 377.2 ([{37Cl}M+H—C4H8]+), 375.2 ([{35Cl}M+H—C4H8]+).

Provenance & Evidence