m-Chloroperbenzoic acid → Tert-butyl 3-[(4-chlorophenyl)sulfinyl]propylcarbamate

HRID 1677005Notes

Reaction equation

HRID 1677005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:25]>ClCCl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:25])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 85937154tert-Butyl 3-[(4-chlorophenyl)thio]propylcarbamate

Product 1

HCID 91057009Tert-butyl 3-[(4-chlorophenyl)sulfinyl]propylcarbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 70 Step B (70 mg) was stirred in 2 mL of dichloromethane with 3-chloroperoxybenzoic acid (MCPBA) (40 mg) for 1 hour at 0° C. An additional 5 mg of MCPBA was added and the reaction stirred 30 minutes more, then diluted with EtOAc and washed with saturated NaHCO3 and brine. The solution was dried over Na2SO4 and concentrated in vacuo to give the titled compound. ESI+ MS: 218 [MH-Boc]+.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialThe solution was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36a7385b049d4a0d9f7250baea14c19f
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

Loading…