Phosphorus pentachloride → HCID 21034892, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)[CH2:6][NH:7][C:8](=O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH:17]([CH2:19][CH3:20])[CH3:18])[CH:11]=1)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl>[CH2:1]([O:3][C:4]([CH:5]1[C:22]2[C:27](=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH:17]([CH2:19][CH3:20])[CH3:18])[CH:11]=2)=[N:7][CH2:6]1)=[O:32])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 3-[2-(3-sec-butoxy-phenyl)-acetylamino]-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (11.2 g, 25.3 mmol) in dichloromethane (140 mL) was added phosphorus pentachloride (7.85 g, 37.7 mmol). The reaction mixture was stirred at room temperature for 15 hrs. The mixture was diluted with dichloromethane and washed with cold saturated aqueous sodium bicarbonate solution (50 mL) and saturated aqueous sodium chloride solution (50 mL). The aqueous phase was extracted with dichloromethane (3×50 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vauo to afford 1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline-4-carboxylic acid ethyl ester (11.0 g, 99% yield) as a yellow oil. The crude product was used in the next step reaction without further purification.