1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acid 3-dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl ester

HRID 2114185Notes

Reaction equation

HRID 2114185 reaction equation
[CH2:1]([NH:3][C:4]([C:6]([C:20](=[O:24])[NH:21][CH2:22][CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][O:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:5])[CH3:2].[CH3:25][N:26]([CH3:55])[C:27]([C:29]1[CH:34]=[C:33](O)[CH:32]=[CH:31][C:30]=1[NH:36][C:37]([C:39]1[C:40]([C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=2)=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:38])=[O:28].CCN=C=NCCCN(C)C>CN(C)C1C=CN=CC=1.CC(C)=O>[CH3:25][N:26]([CH3:55])[C:27]([C:29]1[CH:34]=[C:33]([O:12][C:11](=[O:13])[CH2:10][CH2:9][O:8][CH2:7][C:6]([C:20](=[O:24])[NH:21][CH2:22][CH3:23])([C:4](=[O:5])[NH:3][CH2:1][CH3:2])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:32]=[CH:31][C:30]=1[NH:36][C:37]([C:39]1[C:40]([C:45]2[CH:46]=[CH:47][C:48]([C:51]([F:52])([F:53])[F:54])=[CH:49][CH:50]=2)=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:38])=[O:28]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 587063754'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amideHCID 587063833-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acid

Product 1

HCID 112279903-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acid 3-dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl esterYield 58.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Procedure

4-Dimethylaminopyridine (55 mg), 3-(2,2′-bisethylcarbamoyl-2-phenylethoxy)propionic acid (115 mg) and 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amide (161 mg) were dissolved in acetone (5 mL), and thereto was added WSC (86 mg). The mixture was stirred at room temperature for 3 hours and then concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=4:1→1:0) to give 3-(2,2′-bisethylcarbamoyl-2-phenylethoxy)propionic acid 3-dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl ester (150 mg).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=4:1→1:0)

Sources & evidence

ORD record
ord-05be9f95c79f4ab48a2199e8b9ab2fd5
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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