tert-Butyl hydroperoxide → (R)-N-(2,3-Dichloro-4-ethylsulphinylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2120344Notes

Reaction equation

HRID 2120344 reaction equation
C([O:5]O)(C)(C)C.[Cl:7][C:8]1[C:13]([Cl:14])=[C:12]([S:15][CH2:16][CH3:17])[CH:11]=[CH:10][C:9]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22]>CCCCCCCCCC.C(Cl)(Cl)Cl>[Cl:7][C:8]1[C:13]([Cl:14])=[C:12]([S:15]([CH2:16][CH3:17])=[O:5])[CH:11]=[CH:10][C:9]=1[NH:18][C:19](=[O:27])[C@:20]([OH:26])([CH3:25])[C:21]([F:22])([F:23])[F:24]

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 11268444(R)-N-(2,3-Dichloro-4-ethylsulphanylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 11428877(R)-N-(2,3-Dichloro-4-ethylsulphinylphenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 15600DecaneSolvent

Procedure

t-Butyl hydrogen peroxide (2.4 ml of a 5.5M solution in decane) was added to a solution of (R)-N-[2,3-dichloro-4-ethylsulphanylphenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide Method 1) (0.23 g) and d-10-camphorsulphonic acid (0.018 g) in chloroform (10 ml) and the mixture was stirred for 18 hours. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-50% EtOAc/isohexane to give the title compound (0.22 g) as a white solid. NMR (CDCl3+1 drop DMSO): 1.21-1.28 (m, 3H), 1.71 (s, 3H), 2.77-2.89 (m, 1H), 3.04-3.16 (m, 1H), 7.14 (s, 1H), 7.78 (d, 1H), 8.66 (d, 1H), 9.73 (s, 1H); m/z: 376.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  3. washeluting with 0-50% EtOAc/isohexane

Sources & evidence

ORD record
ord-d1fe87890d094989aa129562db83d535
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

Loading…