Water → HCID 68881567, compound

HRID 2111024Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([NH:13][C:14](=[O:25])[O:15][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH3:17])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].O>CN(C)C=O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:16]([O:15][C:14]([NH:13][C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:7][CH:6]=2)=[N:9][O:10][CH:11]=1)=[O:25])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution (2 ml) of 1-(2-chlorophenyl)ethyl 3-(4-hydroxyphenyl)-4-isoxazolylcarbamate (80 mg, 0.223 mmol) in N,N-dimethylformamide were added potassium carbonate (60 mg, 0.435 mmol) and ethyl 5-bromovalerate (60 mg, 0.287 mmol), and the mixture was stirred at 100° C. for 1 hour. Water was added, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (59 mg, 55%).

Workup

extractionthe mixture was extracted with ethyl acetate
washthe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-a84a5992f2d345af95278620a96c706d
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517996B2

Reaction notes

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