Cesium carbonate → 3,3,3-Trifluoro-2-hydroxy-N-(4-oxazol-2-yl-phenyl)-2-[1-(2-trifluoromethyl-phenyl)-cyclobutylmethyl]-propionamide

HRID 252284Notes

Reaction equation

HRID 252284 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:31])[C:14](=[O:30])[CH2:15][C:16]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:19][CH2:18][CH2:17]2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[SiH](C)C.[F:42][CH:43]([F:45])[F:44].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1>[F:42][C:43]([F:45])([F:44])[C:14]([OH:30])([CH2:15][C:16]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:27])[F:28])[CH2:19][CH2:18][CH2:17]1)[C:13]([NH:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]2[O:1][CH:5]=[CH:4][N:3]=2)=[CH:11][CH:10]=1)=[O:31]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2724141Tetrabutylammonium FluorideHCID 58897678N-(4-Oxazol-2-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamideHCID 131728615HCID 131728615, compound

Product 1

HCID 236415503,3,3-Trifluoro-2-hydroxy-N-(4-oxazol-2-yl-phenyl)-2-[1-(2-trifluoromethyl-phenyl)-cyclobutylmethyl]-propionamideYield 4.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

63 mg (0.15 mmol) of N-(4-oxazol-2-yl-phenyl)-2-oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionamide in 2 ml dimethylformamide is mixed at 0° C. with 48.7 mg (0.15 mmol) of cesium carbonate and 0.14 ml (0.88 mmol) of trimethylsilane-trifluoromethane (CF3.TMS). The reaction mixture was stirred overnight at room temperature. 0.1 ml of 1M tetrabutylammonium fluoride in tetrahydrofuran was added and stirred over the weekend 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 preparative TLC (EtOAc-hexane 30%) to yield 3.3 mg of product.

Workup

  1. stirringstirred over the weekend at room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed twice with water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customThe residue was purified by preparative TLC (EtOAc-hexane 30%)

Sources & evidence

ORD record
ord-cdcd1148c7904e1faf347ffa0bb4c0b1
Source dataset
uspto-grants-2011_01
Patent number
US07868031B2

Reaction notes

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