Potassium Carbonate → HCID 59820853, compound

HRID 1363652Notes

Reaction equation

HRID 1363652 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[CH3:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>O.C(#N)C>[CH3:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][N:16]([C:13]1[CH:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:23])([F:24])[F:1])=[CH:5][CH:6]=2)=[CH:15][CH:14]=1)[C:17](=[O:22])[C:18]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12099m-Xylyl bromideHCID 2855718-Crown-6HCID 59820921Methyl 2-oxo-2-[[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]amino]acetate

Product 1

HCID 59820853HCID 59820853, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl N-[4′-(trifluoromethoxy)biphenyl-4-yl]oxamate (250 mg, 0.737 mmol), 3-methylbenzyl bromide (0.299 ml, 2.21 mmol), potassium carbonate (306 mg, 2.21 mmol), 18-crown-6 (20 mg, 0.074 mmol) and acetonitrile (10 ml) was stirred at 50° for 3 hors under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (320 mg, 98%) as a colorless oil.

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 residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c9fd6fdcdb214d339ed83d184ec18819
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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