Hydrogen Peroxide → (R)-N-(2,3-Dichloro-4-ethylsulphonylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2120345Notes

Reaction equation

OO.[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([S:11]([CH2:13][CH3:14])=[O:12])[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:24])[C@:17]([OH:23])([CH3:22])[C:18]([F:21])([F:20])[F:19].CC[O:27]C(C)=O>O.C(O)(=O)C>[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([S:11]([CH2:13][CH3:14])(=[O:27])=[O:12])[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:24])[C@:17]([OH:23])([CH3:22])[C:18]([F:19])([F:20])[F:21]

Participants

Conditions

Temperature: 95 °C

Procedure

Hydrogen peroxide (15 ml of a 30 wt. % solution in water) was added to a solution of (R)-N-[4-ethylsulphanyl-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 1) (1.88 g) in glacial acetic acid (26 ml) and the mixture was heated at 95° C. for 1.5 hours then cooled. EtOAc (200 ml) was added and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution (4×200 ml) and brine (250 ml) then was dried. Volatile material was removed by evaporation and the residue was purified by chromatography eluting with 0-50% EtOAc/isohexane to give the title compound (1.71 g) as a white solid. NMR: 1.1 (t, 3H), 1.61 (s, 3H), 3.5 (q, 2H), 8.02 (d, 1H), 8.31 (d, 1H); m/z 392.

Workup

temperaturethen cooled
washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution (4×200 ml) and brine (250 ml)
customthen was dried
customVolatile material was removed by evaporation
customthe residue was purified by chromatography
washeluting with 0-50% EtOAc/isohexane

Sources & evidence

ORD record: ord-b1015db10a4b40f09c7a101f7f7d1106
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689909B1

Reaction notes

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