p-Bromobenzenesulfonyl chloride → methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

HRID 29280

Reaction equation

HRID 29280 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:10])[CH:7]([CH3:9])[CH3:8])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 111190Methyl valinate hydrochloride

Product 1

HCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinateYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.838 g of L-valine methyl ester hydrochloride in 15 mL of dichloromethane, cooled in an ice bath, 1.34 g of 4-bromobenzenesulfonyl chloride was added followed by 2.79 mL of triethylamine. The mixture was stirred at room temperature overnight and then diluted with dichloromethane. The dichloromethane was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide 1.77 g of methyl N-[(4-bromophenyl)sulfonyl]-L-valinate as a colorless solid. Yield ˜100%. m.p. 88-90° C.; MS: 348.2 (M−H)−.

Workup

  1. washThe dichloromethane was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7aee23be9fa4d6ea3058bed23397285
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

Loading…