Dichloromethane → (2S)-[5-Chloro-2-(5-dibutylamino-naphthalene-1-sulfonylamino)-benzoylamin o]-3-(2'-phenoxy-biphenyl-4-yl)-propionic acid methyl ester

반응식

[NH2:1][C:2]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:3]=1[C:4]([NH:6][CH:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9])=[O:5].[CH3:36][CH2:37][CH2:38][CH2:39][N:40]([C:45]1[C:50]2[CH:51]=[CH:52][CH:53]=[C:54]([S:55](Cl)(=[O:57])=[O:56])[C:49]=2[CH:48]=[CH:47][CH:46]=1)[CH2:41][CH2:42][CH2:43][CH3:44].[CH2:59](Cl)Cl>>[CH3:59][O:9][C:8](=[O:10])[C@@H:7]([NH:6][C:4](=[O:5])[C:3]1[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:2]=1[NH:1][S:55]([C:54]1[C:49]2[C:50](=[C:45]([N:40]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:39][CH2:38][CH2:37][CH3:36])[CH:46]=[CH:47][CH:48]=2)[CH:51]=[CH:52][CH:53]=1)(=[O:57])=[O:56])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:16][CH:17]=1

참가 물질

반응물 3

HCID 6344Dichloromethane

HCID 191102Bansyl compound

HCID 219215082-(2-Amino-5-chloro-benzoylamino)-3-(2'-phenoxy-biphenyl-4-yl)-propionic acid

생성물 1

HCID 58718025(2S)-[5-Chloro-2-(5-dibutylamino-naphthalene-1-sulfonylamino)-benzoylamin o]-3-(2'-phenoxy-biphenyl-4-yl)-propionic acid methyl ester수율 74%

실험 절차

A solution of 2-(2-amino-5-chloro-benzoylamino)-3-(2′-phenoxy-biphenyl-4-yl)-propionic acid (0.05 g, 0.1 mmol) [prepared by reacting (2S)-amino-3-(2′-phenoxy-biphenyl-4-yl)propionic acid methyl ester hydrochloride salt and 2-amino-5-chlorobenzoic acid by general procedure A] in CH2Cl2 was treated with (0.035 g, 0.1 mmol) of bansyl chloride according to the general procedure F. Product was purified by flash column chromatography on silicagel using ethyl acetate hexanes to give product as pale yellow solid (0.06 g, 74.0% yield).