Pyridine → Methyl 2-[(4-chloro-phenyl)sulfonylamino]-3-trifluoromethyl-4,4,4-trifluorobutanoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-amino-3-(trifluoromethyl)-4,4,4-trifluorobutanoate (2.12 g, 8.87 mmol) in CH2Cl2 (10 mL) was stirred under nitrogen at 25° C. Pyridine (10 mL, 126 mmol) was added dropwise followed by 4-chloro-benzenesulfonyl chloride (2.81 g, 13.3 mmol) in one portion, and the resulting solution stirred for 18 hours at 25° C. After this time period, the reaction was complete by TLC (20:80 EtOAc:PE). After quenching with H2O, the mixture was diluted with Et2O (200 mL). The organic layer was washed with 1 N aq. HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL), and then dried (MgSO4). After concentration, the crude product was purified by Biotage Flash™ 40 chromatography, eluent: 5:95 to 20:80 EtOAc:PE, to obtain methyl 2-[(4-chloro-phenyl)sulfonylamino]-3-trifluoromethyl-4,4,4-trifluorobutanoate as a solid (1.53 g, 42%). Mass Spectrum

Provenance & Evidence