Pyridine → 4,4,4-Trifluoro-2-(3,4,5-trifluoro-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester

HRID 1987587Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[CH2:14]([O:16][C:17](=[O:29])[CH:18]([NH2:28])[CH:19]([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])[CH3:15].N1C=CC=CC=1>C(Cl)Cl>[CH2:14]([O:16][C:17](=[O:29])[CH:18]([NH:28][S:10]([C:4]1[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=1)(=[O:12])=[O:11])[CH:19]([C:20]([F:23])([F:21])[F:22])[C:24]([F:26])([F:27])[F:25])[CH3:15]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3,4,5-trifluorobenzenesulfonyl chloride (0.348 mL, 2.50 mmol) in CH2Cl2 (5 mL) was added to a solution of 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (0.4 g, 1.67 mmol) prepared as described (J. Med Chem. 1981, 24, 1043-1047), and pyridine (0.27 mL, 3.34 mmol) in CH2Cl2 (5 mL) at 0° C. and allowed to warm to 25° C. for 19 h. The solution was washed with 1M HCl (1 mL), brine (1 mL), dried over Na2SO4 and concentrated. The crude solid was purified by Biotage Flash™ chromatography, eluting with EtOAc/hexanes (1:4), to give 4,4,4-trifluoro-2-(3,4,5-trifluoro-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester (0.63 g, 85%) as a white solid. Mass Spectrum (+ESI): 448 [M+H]+.

Workup

customprepared
customat 0° C.
washThe solution was washed with 1M HCl (1 mL), brine (1 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude solid was purified by Biotage Flash™ chromatography
washeluting with EtOAc/hexanes (1:4)

Sources & evidence

ORD record: ord-1590b2338b394edd97caede7f01c24fb
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550629B2

Reaction notes

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