Imidazole → (R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

反応式

[OH:1][CH2:2][C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-:20])=[O:19])[C:9]1=[O:21])[C:4]([O:6][CH3:7])=[O:5].C(Cl)Cl.N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>>[Si:30]([O:1][CH2:2][C@@H:3]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:18]([O-:20])=[O:19])[C:9]1=[O:21])[C:4]([O:6][CH3:7])=[O:5])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

参加物

反応物 4

HCID 795Imidazole

HCID 6344Dichloromethane

HCID 28928tert-Butyldimethylsilyl chloride

HCID 67088204(R)-Methyl 3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

生成物 1

HCID 67088016(R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

実験手順

A round bottom flask was charged with (R)-methyl 3-hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate (4 g, 0.01 mol), methylene chloride (40 mL, 0.5 mol) and 1H-imidazole (1.6 g, 0.023 mol) and tert-butyldimethylsilyl chloride (2.3 g, 0.015 mol) were added at 0° C. and the reaction allowed to warm to room temperature and stirred for 16 h. The reaction mixture was quenched with water and extracted with methylene chloride. Solvent was removed under reduced pressure to recover the pure product as an orange solid. MS m/z=407.5 (M+H).