Pyridine → 2-(4-Chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester

HRID 1987593Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:28])[CH:15]([NH2:27])[CH:16]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:17][C:18]([F:21])([F:20])[F:19].N1C=CC=CC=1>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:28])[CH:15]([NH:27][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:16]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:22][C:23]([F:25])([F:26])[F:24]

Participants

Conditions

Temperature: 25 °C

Procedure

4-Chlorophenyl sulphonyl chloride (85 mg, 0.40 mmol) was added to a solution of 2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester (108 mg, 0.40 mmol) and pyridine (0.15 mL, 1.00 mmol) in CH2Cl2 (2 mL) and the reaction was subsequently stirred for 18 hours at 25° C. The solvent was removed in vacuo and the residue was dissolved in EtOAc (20 mL). This solution was washed with 1M HCl (2×10 mL) and brine (10 mL), dried over Na2SO4 and evaporated to afford a crude oil which was purified by flash chromatography, eluting with 20:80 EtOAc:hexanes, to provide the title compound (125 mg) as an oil in 70% yield. Mass Spectrum (−ESI): 446.0 [M−H]−.

Workup

customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in EtOAc (20 mL)
washThis solution was washed with 1M HCl (2×10 mL) and brine (10 mL)
dry with materialdried over Na2SO4
customevaporated
customto afford a crude oil which
customwas purified by flash chromatography
washeluting with 20:80 EtOAc

Sources & evidence

ORD record: ord-ce9cb1ec664a4fdca9ef043310f58147
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550629B2

Reaction notes

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