Water → 1-(4-Hydroxyphenyl)cyclopropanecarboxylic Acid {4-[3-(acetylmethylamino)pyrrolidin-1-yl]phenyl}amide

반응식

B(Br)(Br)Br.CSC.[C:8]([CH2:11][NH:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3([C:30]4[CH:35]=[CH:34][C:33]([O:36]C)=[CH:32][CH:31]=4)[CH2:29][CH2:28]3)=[O:26])=[CH:20][CH:19]=2)[CH2:14]1)(=[O:10])[CH3:9].O>ClCCl>[C:8]([CH2:11][NH:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25]([C:27]3([C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=4)[CH2:28][CH2:29]3)=[O:26])=[CH:22][CH:23]=2)[CH2:14]1)(=[O:10])[CH3:9]

참가 물질

실험 절차

Boron tribromide-dimethyl sulfide (460 mg) was added to a solution of 1-(4-methoxyphenyl)cyclopropanecarboxylic acid {4-[3-(acetylmethylamino)pyrrolidin-1-yl]phenyl}amide (540 mg) in dichloromethane (5.5 ml) at 0° C. After a reaction time of 12 hours at room temperature, water was added to the mixture, the phases were separated, and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, concentrated and purified by chromatography (silica gel, toluene/ethanol/ethyl acetate 8:1:1 with addition of 0.1% triethylamine). This resulted in the product with the molecular weight of 393.49 (C23H27N3O3); MS(ESI): 394 (M+H+).