Methyl chloroglyoxylate → Methyl 2-oxo-2-[[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]amino]acetate

HRID 1363651Notes

Reaction equation

HRID 1363651 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>ClCCl.O>[F:23][C:22]([F:24])([F:25])[O:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:10][CH:11]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 516892Sodium BicarbonateHCID 27607274'-Trifluoromethoxy-biphenyl-4-ylamine

Product 1

HCID 59820921Methyl 2-oxo-2-[[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]amino]acetateYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl chloroglyoxylate (2.98 ml, 32.4 mmol) in dichloromethane (10 ml) was added dropwise at a slow speed to a mixture of 4-amino-4′-(trifluoromethoxy)biphenyl (5.476 g, 21.6 mmol), sodium hydrogencarbonate (3.62 g, 43.2 mmol), dichloromethane (40 ml) and water (40 ml), and stirred at 0° for 2 hours. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (6.71 g, 91.5%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2b5384987c03430c8f946f4c436ac0cc
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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