Diethyl Ether → HCID 69112935, compound

HRID 841181Notes

Reaction equation

HRID 841181 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:18]=[C:17]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14]=1[NH:26][C:27](=[O:35])[C@:28]([OH:34])([CH3:33])[C:29]([F:32])([F:31])[F:30].CCOCC>ClCCl>[F:12][C:13]1[CH:18]=[C:17]([S:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:9])[CH:16]=[CH:15][C:14]=1[NH:26][C:27](=[O:35])[C@:28]([OH:34])([CH3:33])[C:29]([F:32])([F:30])[F:31]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 54446821HCID 54446821, compound

Product 1

HCID 69112935HCID 69112935, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (55%, 0.157 g) 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 dichloromethane (5 ml) and the mixture was stirred at ambient temperature for 90 minutes. Ether (20 ml) was added and the solution was washed with saturated aqueous sodium carbonate solution (2×10 ml) and brine 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 (0.138 g) as a gum. NMR: 1.55 (s, 3H), 7.5-7.6 (m, 4H), 7.66 (d, 1H), 7.74 (m, 2H), 7.87 (t, 1H), 9.8 (br s, 1H); MS: 374 (M−H)−.

Workup

  1. washthe solution was washed with saturated aqueous sodium carbonate solution (2×10 ml) and brine
  2. customthen dried
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  5. washeluting with 20-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c504ef41c1544ee59ff7d65b114b5abb
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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