Sodium Hydroxide → HCID 67529640, compound

HRID 2261854Notes

Reaction equation

HRID 2261854 reaction equation
C[O:2][C:3](=[O:37])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[N:21]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])[N:22]=[CH:23][C:24]=3[CH:25]([CH3:27])[CH3:26])=[CH:14][C:13]=2[CH3:36])=[CH:8][CH:7]=1.[OH-].[Na+]>O.C1COCC1.CO>[Cl:34][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:35])[C:28]=1[N:21]1[C:20]([CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:37])=[O:2])=[CH:7][CH:8]=3)=[C:13]([CH3:36])[CH:14]=2)=[C:24]([CH:25]([CH3:27])[CH3:26])[CH:23]=[N:22]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67528074HCID 67528074, compound

Product 1

HCID 67529640HCID 67529640, compoundYield 30.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-{4′-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2′-methyl-biphenyl-4-yl}-acrylic acid methyl ester (510 mg, 0.928 mmol), 5 N sodium hydroxide (928 μL, 4.64 mmol), methanol (15 mL) and THF (12 mL) is stirred overnight at room temperature. The reaction mixture is diluted with water and most of the THF and methanol is evaporated. The remaining aqueous portion is washed with ether and the ether layer is discarded. The aqueous layer is acidified with 1 N HCl and extracted with ether. The combined ether layers are washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue is purified using flash chromatography with 5% MeOH/CH2Cl2 and triturated in ether-hexane to give 146 mg (30%) of the title compound. ES/MS m/e (35Cl) 521.3 (M+1)

Workup

  1. customis evaporated
  2. washThe remaining aqueous portion is washed with ether
  3. extractionextracted with ether
  4. washThe combined ether layers are washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified
  8. customtriturated in ether-hexane

Sources & evidence

ORD record
ord-eb0e8fd885e2473fa5a8cfa8fb7967ca
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…