Potassium hydroxy sulfite → (R)-N-[2-Chloro-4-(4-carboxyphenylsulphinyl)phenyl]2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2301035Notes

Reaction equation

HRID 2301035 reaction equation
[OH:1]OS([O-])=O.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[NH:24][C:25](=[O:33])[C@:26]([OH:32])([CH3:31])[C:27]([F:30])([F:29])[F:28]>C([O-])(=O)C.[Na+].CO>[Cl:7][C:8]1[CH:13]=[C:12]([S:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=2)=[O:1])[CH:11]=[CH:10][C:9]=1[NH:24][C:25](=[O:33])[C@:26]([OH:32])([CH3:31])[C:27]([F:30])([F:28])[F:29]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 53644641(R)-N-[2-chloro-4-(4-carboxyphenylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 69749322(R)-N-[2-Chloro-4-(4-carboxyphenylsulphinyl)phenyl]2-hydroxy-2-methyl-3,3,3-trifluoropropanamideYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 517045Sodium AcetateSolvent

Procedure

Oxone (1.47 g) as a solution in 1M sodium acetate solution (12 ml) was added to a mixture of (R)-N-[2-chloro-4-(4-carboxyphenylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 291) (1 g) in methanol (25 ml) and stirred for 2 hours. The reaction mixture was filtered and the solid washed with water and dried under vacuum to give the title compound as a solid (1.02 g) containing 9% of the corresponding sulphone. NMR: 1.6 (s, 3H), 7.75 (d, 1H), 7.8-7.9 (m, 3H), 7.95 (d, 1H), 8.0-8.05 (m, 3H), 8.15 (d, 1H), 9.8 (s, 1H); MS (ESP−); 434.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-7732bd9054154ac3a6c48cded1bbfbad
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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