Sodium hydride → {3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid benzyl ester

HRID 2114180Notes

Reaction equation

HRID 2114180 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:33])[C:5]([C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]([C:17]1[C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:16])=[O:6].Br[CH2:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][O:13][C:11]1[CH:10]=[CH:9][C:8]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[C:7]([C:5](=[O:6])[N:4]([CH3:33])[CH3:3])[CH:12]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 587063754'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amide

Product 1

HCID 58706373{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid benzyl esterYield 56.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (34 mg) was dissolved in THF (9 ml), and the solution was cooled to 0° C. and thereto were added 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amide (300 mg) and tetrabutyl ammonium iodide (10 mg). After addition of benzyl bromoacetate (160 mg), the resulting mixture was stirred at 40° C. for 1 hour. The mixture was stirred at room temperature for 4 hours. The reaction solution was filtered through a Celite, and the filtrate was concentrated and purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to give {3-dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxy}acetic acid benzyl ester (226 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. filtrationThe reaction solution was filtered through a Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-7034289ee51247048f3a4081341a3f08
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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