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

HRID 1720631

반응식

HRID 1720631 반응식
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O.O1CCOCC1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4])(=[O:26])=[O:25])=[CH:22][CH:23]=1

참가 물질

6

반응물 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 69435D-Threonine

생성물 1

HCID 2104039N-[4-methoxybenzenesulfonyl]-(D)-threonine

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of D-threonine (5.0 g, 0.042 mol) in water (50 mL) and dioxane (50 mL) containing triethylamine (8.9 mL, 0.063 mol) at room temperature is added 4-methoxybenzenesulfonyl chloride (9.54 g, 0.046 mol). The reaction mixture is stirred overnight at room temperature. Most of the dioxane is evaporated off, and the pH is adjusted to pH=2 with 1N HCl. The mixture is then extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated in vacuo to provide N-[4-methoxybenzenesulfonyl]-(D)-threonine.

후처리

  1. customMost of the dioxane is evaporated off
  2. extractionThe mixture is then extracted with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e7c47e6c7268461ba2994d7f76342297
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506242

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