Potassium Carbonate → N-(4-Oxazol-2-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamide

HRID 252283Notes

Reaction equation

S(Cl)(Cl)=O.[O:5]=[C:6]([CH2:10][C:11]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[CH2:14][CH2:13][CH2:12]1)[C:7](O)=[O:8].[O:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[O:25]1[CH:29]=[CH:28][N:27]=[C:26]1[C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:7](=[O:8])[C:6](=[O:5])[CH2:10][C:11]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([F:22])([F:23])[F:24])[CH2:14][CH2:13][CH2:12]2)=[CH:32][CH:31]=1

Participants

Conditions

Temperature: -5 °C

Procedure

0.052 ml of thionyl chloride was added to a solution of 0.1 g of 2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acid in 2 ml of dimethyl acetamide at −5° C., and stirred for 30 min at −5° C. Then 56 mg of 4-oxazol-2-yl-phenylamine was added in solid form and stirred for 1 hour at room temperature. Potassium carbonate was added and stirred overnight at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined ethyl acetate extracts were washed twice with water, dried and concentrated by evaporation. The residue was purified by column chromatography on silica-gel (EtOAc-hexane 10%-20%) to yield 63 mg of product.

Workup

stirringstirred for 1 hour at room temperature
stirringstirred overnight at room temperature
customThe reaction was quenched with water
extractionextracted with ethyl acetate
washThe combined ethyl acetate extracts were washed twice with water
customdried
concentrationconcentrated by evaporation
customThe residue was purified by column chromatography on silica-gel (EtOAc-hexane 10%-20%)

Sources & evidence

ORD record: ord-2a9a28c12c124dba82b9156e56a8d837
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868031B2

Reaction notes

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