Triethylamine → N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-D-valine t-butyl ester
Reaktionsgleichung
[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]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 23 °C
Versuchsvorschrift
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.
Aufarbeitung
- washwashed with saturated aqueous NaHCO3, water, aqueous citric acid (1 M), water, brine
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- dissolutionThe residue was dissolved in i-Pr2O
- additionhexane was added which
- customgave a precipitate
- customThe solvents were evaporated in vacuo
- customthe solid was triturated with hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-cda5791dde4d4c8fb06bd8b789694eee
- Quelldatensatz
- uspto-grants-2000_07
- Patentnummer
- US06093731
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