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

HRID 2289809ノート

反応式

HRID 2289809 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
23 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cda5791dde4d4c8fb06bd8b789694eee
出典データセット
uspto-grants-2000_07
特許番号
US06093731

反応ノート

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