Water → (S)-3-(3-bromo-5-methyl-phenylmethanesulfonyl)-2-methyl-propionic acid

HRID 1432105Notes

Reaction equation

HRID 1432105 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([CH3:16])[CH:15]=1)[CH2:5][S:6][CH2:7][C@@H:8]([CH3:12])[C:9]([OH:11])=[O:10].[OH:17]OS([O-])=O.[K+].[OH2:23]>C(#N)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][S:6]([CH2:7][C@@H:8]([CH3:12])[C:9]([OH:11])=[O:10])(=[O:17])=[O:23])[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 68541731(S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

Product 1

HCID 68544363(S)-3-(3-bromo-5-methyl-phenylmethanesulfonyl)-2-methyl-propionic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6.48 g (21 mmol) (S)-3(3-bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid in 70 ml acetonitrile and 35 ml water is added 65.7 g (107 mmol) oxone®. After stirring for 2.5 hrs at rt the mixture is diluted with EtOAc and water to get a clear solution. The organic layer is washed with brine, dried over magnesium sulfate and the solvent is evaporated. Crystallization from DCM/diethyl ether and a little methanol gives the title compound as white crystals.

Workup

  1. customto get a clear solution
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is evaporated
  5. customCrystallization from DCM/diethyl ether

Sources & evidence

ORD record
ord-c78b10a65d354cc1a6d0bd5d59691815
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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