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

HRID 1245104

Reaction equation

HRID 1245104 reaction equation
[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

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 191102Bansyl compoundHCID 219215082-(2-Amino-5-chloro-benzoylamino)-3-(2'-phenoxy-biphenyl-4-yl)-propionic acid

Product 1

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

Procedure

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).

Workup

  1. customProduct was purified by flash column chromatography on silicagel

Sources & evidence

ORD record
ord-3324280800134e06b46e14dc221a2c32
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Linked notes

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