Water → methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

HRID 606507

Reaction equation

HRID 606507 reaction equation
Cl.[NH2:2][C@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH:4]([CH3:6])[CH3:5].C(=O)([O-])[O-].[Na+].[Na+].O.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CC(C)=O>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:2][C@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH:4]([CH3:6])[CH3:5])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 111190Methyl valinate hydrochloride

Product 1

HCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinateYield 84.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of methyl valinate hydrochloride (10.0 g, 59.7 mmol) and sodium carbonate (15.8 g, 149 mmol) in acetone (200 ml)-water (100 mL) was added 4-bromobenzenesulfonyl chloride (12.7 g, 49.7 mmol) at 0° C., and the mixture was stirred at room temperature for 12 hr after addition. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with 0.1N hydrochloric acid, water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from hexane-ethyl acetate to give the title compound as a white powder (14.7 g, 84%).

Workup

  1. additionafter addition
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with 0.1N hydrochloric acid, water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-18a2087bacef4f858c652956d4472523
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Linked notes

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