Hydrochloric Acid → HCID 68983174, compound

HRID 475577Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][CH:23]([C:28]([C:30]3[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][N:31]=3)=[O:29])C(OC)=O)[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1.Cl>C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][CH2:23][C:28]([C:30]3[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][N:31]=3)=[O:29])[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A 5.5 g quantity of methyl 2-[2-(3-benzyloxy-4-methoxy phenyl)oxazol-4-ylmethyl]-3-(3-methylpyridin-2-yl)-3-oxopropionate obtained in Example 135 was dissolved in 20 ml of ethanol, 80 ml of a 5N aqueous hydrochloric acid solution was added thereto, and the mixture was stirred with heating at 80° C. for 1.5 hours. While stirring with ice cooling, the reaction mixture was neutralized with 5 N aqueous sodium hydroxide solution, and ethyl acetate extraction was performed. The organic layer was washed twice with water, concentrated under reduced pressure, and the obtained crude crystals were recrystallized with a mixture of 20 ml of ethanol and 40 ml of n-hexane, thereby yielding 1.92 g of pale yellow powdery 3-[2-(3-hydroxy-4-methoxy phenyl)oxazol-4-yl]-1-(3-methylpyridin-2-yl)propan-1-one.

Workup

stirringWhile stirring with ice cooling
extractionthe reaction mixture was neutralized with 5 N aqueous sodium hydroxide solution, and ethyl acetate extraction
washThe organic layer was washed twice with water
concentrationconcentrated under reduced pressure
customthe obtained crude crystals
customwere recrystallized with a mixture of 20 ml of ethanol and 40 ml of n-hexane

Sources & evidence

ORD record: ord-2406f2c3f5a74443a6ebcb58ec877315
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637559B2

Reaction notes

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