Ethyl Acetate → HCID 136167183, compound

HRID 1891129Notes

Reaction equation

HRID 1891129 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7](=[O:44])[C:8]1[CH:13]=[C:12]([C:14]2[O:18][N:17]=[C:16]([CH3:19])[C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:11]([O:28]CC2C=CC=CC=2)=[CH:10][C:9]=1[O:36]CC1C=CC=CC=1.C(OCC)(=O)C>CO.[Pd]>[CH3:5][O:6][C:7](=[O:44])[C:8]1[CH:13]=[C:12]([C:14]2[O:18][N:17]=[C:16]([CH3:19])[C:15]=2[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:11]([OH:28])=[CH:10][C:9]=1[OH:36]

Participants

6

Reactant 3

HCID 8857Ethyl Acetate2×HCID 2723923Ammonium formateHCID 59264806HCID 59264806, compound

Product 1

HCID 136167183HCID 136167183, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Ammonium formate (172 mg, 20 eq) was added to a solution of 2,4-Bis-benzyloxy-5-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzoic acid methyl ester (72 mg, 0.13 mmol) in methanol (2 ml)/ethyl acetate (1 ml) under a nitrogen atmosphere. 10% Palladium on carbon (cat.) was added and the suspension heated at 60° C. overnight. The solution was allowed to cool. Ethyl acetate (5 ml) added, solution washed with water (2×5 ml) and saturated aqueous sodium chloride solution (5 ml). The solution was dried over anhydrous magnesium sulphate and concentrated. The crude products were purified by column chromatography, silica, eluting with ethyl acetate in hexane (gradient 25% to 45% ethyl acetate) to give 2,4-dihydroxy-5-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzoic acid methyl ester (7.0 mg).

Workup

  1. temperatureto cool
  2. washsolution washed with water (2×5 ml) and saturated aqueous sodium chloride solution (5 ml)
  3. dry with materialThe solution was dried over anhydrous magnesium sulphate
  4. concentrationconcentrated
  5. customThe crude products were purified by column chromatography, silica
  6. washeluting with ethyl acetate in hexane (gradient 25% to 45% ethyl acetate)

Sources & evidence

ORD record
ord-12c4f21be085481e99f5fadb32329f81
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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