Methyl chloroglyoxylate → HCID 58007715, compound

HRID 1667640Notes

Reaction equation

HRID 1667640 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][C:9]1[CH:10]=[C:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>ClCCl.O>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]([C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=3)=[CH:10][C:9]=2[NH:8][C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:18][CH:19]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 516892Sodium BicarbonateHCID 59820844HCID 59820844, compound

Product 1

HCID 58007715HCID 58007715, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl chloroglyoxylate (184 μl, 2.0 mmol) in dichloromethane (1.5 ml) was added dropwise at a slow speed to a mixture of 3-amino-4-[4-(tert-butyl)benzyloxy]-4′-(trifluoromethoxy)biphenyl (415 mg, 1.0 mmol), sodium hydrogencarbonate (168 mg, 2.0 mmol), water (5 ml) and dichloromethane (7 ml), and the mixture was stirred at 0° C. 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 (456 mg, 90.9%) 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-d87cd1c23d1e49a082984767016b954c
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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