Triethylamine → N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-D-valine t-butyl ester

HRID 2289809노트

반응식

HRID 2289809 반응식
[C:1]([O:5][C:6](=[O:12])[C@@H:7]([CH:9]([CH3:11])[CH3:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[Cl:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([S:31](Cl)(=[O:33])=[O:32])[CH:29]=2)[C:24]([Cl:35])=[CH:23][N:22]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]([CH:9]([CH3:10])[CH3:11])[NH:8][S:31]([C:28]1[CH:29]=[C:30]2[C:25]([C:24]([Cl:35])=[CH:23][N:22]=[C:21]2[Cl:20])=[CH:26][CH:27]=1)(=[O:33])=[O:32])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 6931638tert-butyl D-valinateHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chloride

생성물 1

HCID 16658807N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-D-valine t-butyl ester수율 72.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
23 °C

실험 절차

D-Valine t-butyl ester (354 mg, 1.69 mmol) and then NEt3 (0.59 mL, 4.2 mmol) were added to a stirred solution of 1,4-dichloro-7-isoquinolinesulphonyl chloride (500 mg, 1.69 mmol) and in CH2Cl2 (20 mL) and the mixture was stirred at 23° C. for 16 h. The mixture was diluted with CH2Cl2 (50 mL), washed with saturated aqueous NaHCO3, water, aqueous citric acid (1 M), water, brine, dried (MgSO4) and evaporated in vacuo. The residue was dissolved in i-Pr2O and hexane was added which gave a precipitate. The solvents were evaporated in vacuo and the solid was triturated with hexane to give N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-D-valine t-butyl ester (532 mg, 1.22 mmol) as a white solid. An analytical sample was obtained by recrystallisation from hexane.

후처리

  1. washwashed with saturated aqueous NaHCO3, water, aqueous citric acid (1 M), water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in i-Pr2O
  5. additionhexane was added which
  6. customgave a precipitate
  7. customThe solvents were evaporated in vacuo
  8. customthe solid was triturated with hexane

출처 및 근거

ORD 기록
ord-cda5791dde4d4c8fb06bd8b789694eee
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06093731

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