Methanesulfonyl chloride → HCID 86635134, compound

HRID 1878398Notes

Reaction equation

HRID 1878398 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([NH:10][C:11](=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([OH:22])[CH:19](C)[CH3:20])[CH:13]=1)([CH3:9])([CH3:8])[CH3:7]>ClCCl>[CH3:1][S:2]([O:22][CH:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:11](=[O:23])[NH:10][C:6]([CH3:9])([CH3:8])[CH3:7])[CH:13]=1)[CH2:19][CH3:20])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66878475HCID 66878475, compound

Product 1

HCID 86635134HCID 86635134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (165 mg, 1.44 mmol) in dichloromethane (2.0 mL) was added to a stirred solution of N-tert-butyl-3-(1-hydroxy-2-methylpropyl)benzamide (300 mg, 1.20 mmol) in dichloromethane (8.0 mL). After 1.5 hours stirring, the mixture was partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum to afford the intermediate 1-(3-(tert-butylcarbamoyl)phenyl)propyl methanesulfonate.

Workup

  1. customthe mixture was partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-785ce14ec30445a49d59ec3fac58db43
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…