C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:32]=[CH:31][CH:30]=[CH:29][C:15]=2[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[CH3:9].B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:32]=[CH:31][CH:30]=[CH:29][C:15]=2[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[CH3:9]Crude 2-{[2-(3-methoxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide (derived via Procedure C from 200 mg resin) is dissolved in 3 mL of dichloromethane and treated with 0.5 mL of 1 M of boron tribromide in dichloromethane for 16 h. Methanol (3 mL) is carefully added and the volatiles are removed. The crude residue is purified via semi-preparative HPLC to give 2-{[2-(3-hydroxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide (28 mg). MS: m/z 417 (m+H).
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