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

HRID 742018노트

반응식

HRID 742018 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffb4a8a670de40a5b54566af8288d822
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552419

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