2,2,2-Trifluoroethanol → HCID 59543721, compound

HRID 1697591Notes

Reaction equation

HRID 1697591 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].[C:13]([C:15]1([NH:18][C:19]([C@@H:21]2[CH2:25][C@@H:24]([S:26]([C:29]3[CH:34]=[CH:33][C:32](F)=[CH:31][C:30]=3[C:36]([F:39])([F:38])[F:37])(=[O:28])=[O:27])[CH2:23][N:22]2[C:40]2[N:41]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:54])[F:53])=[CH:48][CH:47]=3)[N:42]=[C:43]([CH3:45])[CH:44]=2)=[O:20])[CH2:17][CH2:16]1)#[N:14].C(OC(C)=O)(C)C>CN(C)C(=O)C>[C:13]([C:15]1([NH:18][C:19]([C@@H:21]2[CH2:25][C@@H:24]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:31][C:30]=3[C:36]([F:37])([F:38])[F:39])(=[O:27])=[O:28])[CH2:23][N:22]2[C:40]2[N:41]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([F:55])([F:54])[F:53])=[CH:48][CH:47]=3)[N:42]=[C:43]([CH3:45])[CH:44]=2)=[O:20])[CH2:16][CH2:17]1)#[N:14]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 7915Isopropyl AcetateHCID 10796Cesium carbonateHCID 46945410HCID 46945410, compound

Product 1

HCID 59543721HCID 59543721, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
40 °C

Procedure

2,2,2-Trifluoroethanol (2.2 ul, 29 umol) and cesium carbonate (9 mg, 29 umol) were added to a solution of (2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide (15 mg, 24 umol; example 267c) in N,N-dimethylacetamide (0.2 ml) under an argon atmosphere. The mixture was stirred for 12 h at ambient temperature and for 5 h at 40° C. Ice water/0.1 N aqueous HCl solution 1/1 and iPrOAc were added and the layers were separated. The aqueous layer was extracted one more time with iPrOAc, the combined organic layers were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a yellow oil which was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (7 mg, 9.9 umol; 44%) as colorless oil. MS (ESI): m/z=710.1 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted one more time with iPrOAc
  3. washthe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto give a yellow oil which
  7. customwas purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-79787c6c630f46adbf72cf9241a3a440
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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