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Potassium Carbonate → n-(4-Oxazol-5-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamide

HRID 1393913
Notes
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Reaction equation

HRID 1393913 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]([OH:9])=O.[O:25]1[C:29]([C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=2)=[CH:28][N:27]=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[O:25]1[C:29]([C:30]2[CH:31]=[CH:32][C:33]([NH:36][C:7](=[O:9])[C:6](=[O:5])[CH2:10][C:11]3([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:21]([F:22])([F:23])[F:24])[CH2:14][CH2:13][CH2:12]3)=[CH:34][CH:35]=2)=[CH:28][N:27]=[CH:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 5177474-(1,3-Oxazol-5-yl)anilineHCID 596809512-Oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acid

Product 1

HCID 16738962n-(4-Oxazol-5-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamideYield 42.1%

Reagents, catalysts & solvents

1
HCID 31374DimethylacetamideSolvent

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-5-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

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

Sources & evidence

ORD record
ord-4a056b89f30c41108fa62d640dfa783d
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348322B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes