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

HRID 1006091노트

반응식

HRID 1006091 반응식
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.O1CCCC1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:1][C@H:2]([CH:3]([CH3:5])[CH3:4])[C:6]([OH:8])=[O:7])(=[O:31])=[O:30])=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 71563D-Valine

생성물 1

HCID 1133588N-[4-methoxybenzenesulfonyl]-(D)-valine수율 73,207.602%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an ice-cooled solution of D-valine (50.5 g, 0.43 mol) and triethylamine (145 mL, 1.034 mol) in a 1:1 mixture of tetrahydrofuran and water (350 mL) was added 4-methoxybenzenesulfonyl chloride (88.2 g, 0.43 mmol). The reaction mixture was stirred and allowed to warm to room temperature overnight. The volatile organics were removed and the aqueous phase was extracted with diethyl ether. The aqueous phase was acidified to pH 3 with 10% hydrochloric acid and the product was extracted into ethyl acetate. The ethyl acetate layer was washed with brine, dried over magnesium sulfate, and then concentrated to give 2(R)-(4-methoxy-benzenesulfonylamino)-3-methylbutyric acid as a white solid (90.45 g).

후처리

  1. customThe volatile organics were removed
  2. extractionthe aqueous phase was extracted with diethyl ether
  3. extractionthe product was extracted into ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d6f7a4467ee54758b685c1a50a932b3c
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787559B2

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