Acetonitrile → HCID 57518506、化合物

反応式

[H-].[Na+].[N:3]1[NH:4][CH:5]=[C:6]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:7]=12.[CH:18]1([S:21](Cl)(=[O:23])=[O:22])[CH2:20][CH2:19]1.[C:25](#N)[CH3:26]>>[CH:18]1([S:21]([N:4]2[CH:5]=[C:6]3[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:7]3=[N:3]2)(=[O:23])=[O:22])[CH2:26][CH2:25][CH2:19][CH2:20]1.[CH:18]1([S:21]([N:3]2[C:7]3[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:6]=3[CH2:5][NH:4]2)(=[O:23])=[O:22])[CH2:26][CH2:25][CH2:19][CH2:20]1

参加物

反応物 4

HCID 6342Acetonitrile

HCID 24758Sodium hydride

HCID 2760919Cyclopropanesulfonyl chloride

HCID 178451520HCID 178451520、化合物

生成物 2

HCID 57518506HCID 57518506、化合物

HCID 67036470HCID 67036470、化合物

実験手順

To a suspension of sodium hydride (60% dispersion in oil, 1.55 g, 38.7 mmol) in anhydrous acetonitrile (200 mL) was added to tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (5.3 g, 25.5 mmol) in one portion under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 2 h. To the resulting white suspension was slowly added cyclopropanesulfonyl chloride (6.9 g, 49.1 mmol) and the mixture was stirred at room temperature for 18 h, quenched with water (120 mL) and the layers were separated. The aqueous layer was then extracted with dichloromethane (2×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified on silica chromatography (300 g Biotage™ column) and eluted with 15-80% ethyl acetate in hexanes to yield the title compound and tert-butyl 1-(cyclopentylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate as a white solid. LC/MS: 314.2 (M+1).