4-Methoxybenzenesulfonyl chloride → N-[4-methoxybenzenesulfonyl]-(D)-valine

HRID 742018Notes

Reaction equation

HRID 742018 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].O1CCOCC1.O.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 71563D-ValineHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 1133588N-[4-methoxybenzenesulfonyl]-(D)-valine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of D-valine (15.0 g, 128.0 mmol) in 1:1 dioxane/water (200 mL) containing triethylamine (19.4 g, 192.0 mmol) at room temperature is added 4-methoxybenzenesulfonyl chloride (29.0 g, 141.0 mmol), and the reaction mixture is stirred at room temperature overnight. The mixture is then diluted with methylene chloride, washed with 1N aqueous hydrochloric acid and water. The organic layer is washed again with brine, dried (Na2SO4), and the solvent is evaporated to provide N-[4-methoxybenzenesulfonyl]-(D)-valine as a crude product. A :solution of this crude product (15.0 g) in toluene (100 mL) containing N,N-dimethylformamide di-t-butyl acetal (50 mL, 206.5 mmol) is heated to 95° C. for 3 hours. The solvent is then evaporated. The crude product is purified by silica gel chromatography (30% ethyl acetate/hexanes) to provide N-[4-methoxybenzenesulfonyl]-(D)-valine t-butyl ester.

Workup

  1. washwashed with 1N aqueous hydrochloric acid and water
  2. washThe organic layer is washed again with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-ffb4a8a670de40a5b54566af8288d822
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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