Hydrogen Peroxide → HCID 69113599, compound

HRID 841180Notes

Reaction equation

OO.[F:3][C:4]1[CH:9]=[C:8]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:17][C:18](=[O:26])[C@:19]([OH:25])([CH3:24])[C:20]([F:23])([F:22])[F:21].C(OCC)(=[O:29])C.[OH2:33]>C(O)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([S:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)(=[O:29])=[O:33])[CH:7]=[CH:6][C:5]=1[NH:17][C:18](=[O:26])[C@:19]([OH:25])([CH3:24])[C:20]([F:23])([F:21])[F:22]

Participants

Conditions

Temperature: 100 °C

Procedure

Hydrogen peroxide (0.2 ml of a 30 wt. % solution in water) was added to a solution of (R)-N-[2-fluoro-4-(phenylthio)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 7) (0.212 g) in glacial acetic acid (0.5 ml) and the mixture was stirred and heated at 100° C. for 75 minutes then allowed to cool. Ethyl acetate (20 ml) was added and the solution was washed with water (20 ml), saturated sodium hydrogen carbonate solution (10 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 20-30% ethyl acetate/hexane to give the title compound (0.155 g) as a solid. M.p. 121-122° C.; NMR: 1.58 (s, 3H), 7.58-7.7 (m, 4H), 7.8 (d, 1H), 7.9-8.05 (m, 4H), 9.8 (brs, 1H); MS: 390 (M−H)−; EA: C16H13F4NO4S 0.5H2O requires C, 48.0; H, 3.5; N, 3.5%; found: C, 47.8; H, 3.5; N, 3.4%.

Workup

temperatureto cool
washthe solution was washed with water (20 ml), saturated sodium hydrogen carbonate solution (10 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 20-30% ethyl acetate/hexane

Sources & evidence

ORD record: ord-7c6ccfe4e60a4f01ae01334daec3a154
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369273B1

Reaction notes

Loading…