4-Methoxybenzenesulfonyl chloride → N-(4-methoxybenzenesulfonyl)-D-valine benzyl ester

HRID 843693Notes

Reaction equation

HRID 843693 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]([CH:13]([CH3:15])[CH3:14])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>O.O1CCOCC1>[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]([CH:13]([CH3:14])[CH3:15])[NH:12][S:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:31][CH:30]=1)(=[O:34])=[O:33])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 56777379D-valine benzyl ester hydrochloride

Product 1

HCID 15429254N-(4-methoxybenzenesulfonyl)-D-valine benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of D-valine benzyl ester hydrochloride (2.4 grams, 10 mmol) and triethylamine (2.5 grams, 3.5 mL, 25 mmol) in water (50 mL) and 1,4-dioxane (50 mL) is added 4-methoxybenzenesulfonyl chloride (2.3 grams, 11 mmol). The mixture was stirred at room temperature for 1 hour and then most of the solvent was removed by evaporation under vacuum. The mixture was diluted with ethyl acetate and was washed successively with dilute hydrochloric acid solution, water and brine. The organic solution was dried over magnesium sulfate and concentrated to leave N-(4-methoxybenzenesulfonyl)-D-valine benzyl ester as a white solid, 3.6 grams (97%); m.p. 92-94° C.

Workup

  1. custommost of the solvent was removed by evaporation under vacuum
  2. additionThe mixture was diluted with ethyl acetate
  3. washwas washed successively with dilute hydrochloric acid solution, water and brine
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ce1d5d7394b4f5088d16dda77efb310
Source dataset
uspto-grants-2002_04
Patent number
US06380219B1

Reaction notes

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