Acetamide → HCID 22013898, compound

HRID 1532733Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](O)=[O:25])=[CH:18][CH:17]=1.S(Cl)(Cl)=O.[C:31]([NH2:34])(=[O:33])[CH3:32]>CO>[C:31]([NH:34][C:24](=[O:25])[CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:21][CH:20]=1)(=[O:33])[CH3:32]

Participants

Conditions

Temperature: 100 °C

Procedure

To 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid (1.50 g, 4.27 mmol) obtained in Example 17 was added thionyl chloride (2.0 ml), and the mixture was stirred under heating for 1 hr at 100° C. Excess thionyl chloride was evaporated under reduced pressure and acetamide (504 mg, 8.54 mmol) was added to the obtained residue. The mixture was stirred under heating for 1 hr at 120° C. Methanol (5 ml) was added, and the reaction mixture was stirred for 10 min and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:1) to give the title compound (541 mg, yield 32%) as a white solid.

Workup

additionwas added to the obtained residue
stirringThe mixture was stirred
temperatureunder heating for 1 hr at 120° C
stirringthe reaction mixture was stirred for 10 min
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-e6459c9b4e00477e8701d89ceda894b8
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06204277B1

Reaction notes

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