Benzyl azide → HCID 136384027、化合物

反応式

[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[N:15][S:14][C:9]2=[C:10]([C:12]#[CH:13])[N:11]=1)=[O:5])[CH3:2].[CH2:25]([N:32]=[N+:33]=[N-:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CCO.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:16]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[N:15][S:14][C:9]2=[C:10]([C:12]2[N:34]=[N:33][N:32]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:13]=2)[N:11]=1)=[O:5])[CH3:2]

参加物

実験手順

To a mixture of 3-(4-chloro-phenyl)-7-ethynyl-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (0.106 mmol) and CH2Cl2/H2O (1/1, 0.70 mL) was added benzylazide (0.117 mmol), CuSO4.5H2O (0.0053 mmol) and sodium L-ascorbate (0.0159 mmol). The mixture was stirred at rt for 16 h before it was partitioned between H2O (20 mL) and CH2Cl2 (20 mL). The aqueous phase was then extracted with CH2Cl2 (2×15 mL). The combined organic layers were washed with brine and water, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 0-20% EtOAc/CH2Cl2, to give the title compound (40 mg) as a white solid: MS (m/z) 492.1 (M+1).