Methanol → HCID 58765742, compound

HRID 860680Notes

Reaction equation

HRID 860680 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH:30]([CH3:32])[CH3:31])[CH3:14])=[CH:7][C:6]=1[CH3:33].[OH-].[Li+].O1CCCC1.CO>Cl.O>[CH:30]([C:16]1[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=2)[O:19][C:15]=1[CH:13]([CH3:14])[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:34])=[O:2])=[C:6]([CH3:33])[CH:7]=1)([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69358489HCID 69358489, compound

Product 1

HCID 58765742HCID 58765742, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

(4-{2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propoxy}-2-methyl-phenyl)-acetic acid methyl ester (0.065 g, 0.1367 mmol), lithium hydroxide (0.020 g, 0.8333 mmol) and 3:2:1 tetrahydrofuran:methanol:water (15 mL) is stirred at 60 deg C. 1 hr. The mixture is cooled on ice/water and diluted with 0.2 N aqueous hydrochloric acid. The product is extracted to ethyl acetate (2×50 mL), the extracts combined, dried over anhydrous magnesium sulfate, filtered and concentrated to afford the title compound as a white solid, 55 mg, 87%. MS M++1 462. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. custom1 hr
  2. temperatureThe mixture is cooled on ice/water
  3. extractionThe product is extracted to ethyl acetate (2×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6a1bd180cd25425a8b15d0ffe4122997
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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