Ethyl Acetate → HCID 136167183, compound

HRID 646460Notes

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

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

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

Sources & evidence

ORD record: ord-779501e964344f218696ed5aeeee6251
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705027B2

Reaction notes

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