Hydrochloric Acid → HCID 21034936, compound

Reaction equation

[CH2:1]([O:3][C:4](=[O:38])[N:5]([CH:12]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:23]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)[CH2:6][CH:7](OC)OC)[CH3:2].Cl>CC(C)=O.O>[CH2:1]([O:3][C:4]([N:5]1[CH:6]=[CH:7][C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:25]([O:28][CH3:29])[CH:26]=2)[CH:12]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)=[O:38])[CH3:2]

Participants

Procedure

[1-(3-Benzyloxy-4-methoxy-phenyl)-2-(3-methoxy-phenyl)-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester (3.15 g, 6.01 mmol) was dissolved in acetone (125 mL) at 0° C., and 6M aqueous hydrochloric acid (25 mL) was added dropwise. After the addition was complete, the mixture was stored at 0° C. overnight (14 hours). The mixture was warmed to room temperature and stirred×4 hours. The mixture was cooled in an ice bath and diluted with water (150 mL). The mixture was extracted with ethyl acetate (3×60 mL). The combined organic extracts were washed with water (60 mL), saturated aqueous sodium chloride solution (60 mL) and dried over anhydrous magnesium sulfate. Concentration of the solvent gave an oily solid that was crystallized from ethyl acetate/hexanes to give 7-benzyloxy-6-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (1.32 g, 2.87 mmol, 48%) as a white solid.