Sodium Bicarbonate → 3-Ethoxycarbonyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenylacetic acid

HRID 494412Notes

Reaction equation

HRID 494412 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[F:17][C:18]([F:35])([F:34])[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]([C:31](Cl)=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>>[CH2:15]([O:14][C:12]([C:3]1[CH:4]=[C:5]([CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:31]([C:26]1[C:25]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:34])[F:35])=[CH:20][CH:21]=2)=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:32])=[O:13])[CH3:16]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chlorideHCID 230332264-Amino-3-ethoxycarbonylphenylacetic acid

Product 1

HCID 576832253-Ethoxycarbonyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenylacetic acidYield 58.6%

Procedure

The 4-amino-3-ethoxycarbonylphenylacetic acid (1.51 g) obtained in Example 9-4d) and 4′-trifluoromethylbiphenyl-2-carboxylic acid chloride (1.99 g) were subjected to reactions similar to those in Example 7a) with the proviso that sodium bicarbonate was used as a base, thereby the title compound (1.87 g) was given as a pale yellow amorphous powder.

Sources & evidence

ORD record
ord-fb2b296aa2754abe931bcb572cfd87e1
Source dataset
uspto-grants-2009_05
Patent number
US07538140B2

Reaction notes

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