Acetic Anhydride → HCID 66812510, compound

HRID 1099567Notes

Reaction equation

[CH2:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]([NH:14][CH2:15][C:16]([OH:18])=[O:17])=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)[CH3:2].C(OC(=O)C)(=O)C>C(OCC)(=O)C>[CH2:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:20]=[CH:19][C:11]([C:12]3[O:17][C:16](=[O:18])[CH2:15][N:14]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-[4-(4-ethylphenoxy)benzoyl]glycine (200 mg, 0.668 mmol) prepared in Example 89 (89a) and acetic anhydride (0.38 mL, 4.03 mmol) was stirred at 80° C. for 20 minutes. Ethyl acetate was added to the reaction mixture, and then the mixture was cooled to room temperature. The solvent was evaporated, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1, v/v) to give 2-[4-(4-ethylphenoxy)phenyl]-1,3-oxazol-5(4H)-one (120 mg, 0.427 mmol). All of this 2-[4-(4-ethylphenoxy)phenyl]-1,3-oxazol-5(4H)-one was dissolved in benzene (0.9 mL), and then 4-isopropoxybenzaldehyde (71 mg, 0.432 mmol) and triethylamine (24 μL, 0.172 nmol) were added thereto. The mixture was stirred at 90° C. for 2 hours. After the addition of water to the reaction solution, the mixture was extracted with a solvent mixture of hexane and ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated to give 181 mg of the title compound (brown oil, yield: 99%).

Workup

temperaturethe mixture was cooled to room temperature
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record: ord-407b6f5572d44854961ce6b6d1251c6a
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143446B2

Reaction notes

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