Hydrogen Peroxide → HCID 54065366, compound

HRID 1062416Notes

Reaction equation

OO.[Cl:3][C:4]1[CH:9]=[C:8]([S:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22].C(OCC)(=[O:30])C.[OH2:34]>C(O)(=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)(=[O:30])=[O:34])[CH:7]=[CH:6][C:5]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:23])([F:24])[F:22]

Participants

Conditions

Temperature: 100 °C

Procedure

Hydrogen peroxide (0.3 ml of a 30 wt. % solution in water) was added to a solution of (R)-N-[2-chloro-4-(4-fluorophenylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 188) (0.283 g) in glacial acetic acid (1.0 ml) and the mixture was stirred and heated at 100° C. for 80 minutes then allowed to cool. Ethyl acetate (40 ml) was added and the solution was washed with water (20 ml), saturated aqueous sodium hydrogen carbonate solution (20 ml) and brine and then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-25% ethyl acetate/hexane to give the title compound (0.261 g; 72%) as a solid Mp 131-133 ° C.; NMR: 1.6 (s, 3H), 7.46 (t, 2H), 8.0 (dd, 1H), 8.08 (m, 2H), 8.15 (d, 1H), 8.3 (d, 1H), 9.85 (brs, 1H); MS (ESP+): 426 (M+H)+.

Workup

temperatureto cool
washthe solution was washed with water (20 ml), saturated aqueous sodium hydrogen carbonate solution (20 ml) and brine
customdried
customVolatile material was removed by evaporation
customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
washeluting with 0-25% ethyl acetate/hexane

Sources & evidence

ORD record: ord-dc1b890f8e924ac6b0eae12408d378eb
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960688B2

Reaction notes

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