Hydrochloric Acid → HCID 74010625, compound

HRID 2247442Notes

Reaction equation

HRID 2247442 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH3:4].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.[H-].[Na+].Cl>O1CCCC1>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:14]=2)=[CH:6][C:5]=1[C:3](=[N:2][O:1][CH2:29][C:28]1[CH:27]=[CH:26][C:25]([C:24]([F:23])([F:33])[F:34])=[CH:32][CH:31]=1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 72534040HCID 72534040, compound

Product 1

HCID 74010625HCID 74010625, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9 mg of [3′-(1-Hydroxyiminoethyl)-4′-methoxybiphenyl-3-yl]acetic acid was dissolved in 0.2 mg of tetrahydrofuran, then 25 mg of 4-trifluoromethylbenzyl bromide and 10 mg of sodium hydride were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was neutralized with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by reverse-phase high performance liquid chromatography to give 5.21 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by reverse-phase high performance liquid chromatography

Sources & evidence

ORD record
ord-c8179295526248d5b0bf8458831309d3
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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