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

HRID 2209665Notes

Reaction equation

HRID 2209665 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.

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-43e6cd8ed76b441bb81256e036b4ef6a
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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