HCID 86732257, compound → HCID 86732258, compound

HRID 930419Notes

Reaction equation

HRID 930419 reaction equation
[CH3:1][C:2]([S@:5]([NH:7][C@:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[F:25])([CH2:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])=[O:6])([CH3:4])[CH3:3]>CC(O)C>[CH3:4][C:2]([S@:5]([NH:7][C@:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[F:25])([CH2:11][C@H:12]([OH:17])[C:13]([F:15])([F:14])[F:16])[CH2:9][F:10])=[O:6])([CH3:1])[CH3:3]

Participants

3

Reactant 1

HCID 86732257HCID 86732257, compound

Product 1

HCID 86732258HCID 86732258, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ru[p-cymeme](1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (2.365 g, 3.94 mmol) was added in one portion to a solution of (R)-2-methyl-N-((S)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)-4-oxopentan-2-yl)propane-2-sulfinamide (3.80 g, 9.86 mmol) in IPA (100 ml) (which had been degassed by bubbling nitrogen through the solution for 30 minutes prior to use) under N2 atmosphere. The reaction was stirred at rt for 2 h. The reaction went to completion. The reaction was quenched with saturated NaHCO3, extracted with EtOAc and the combined organic extracts were washed with water, brine, dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-40% EtOAc/hexanes to afford a light brown solid as (R)-2-methyl-N-((2S,4S)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)-4-hydroxypentan-2-yl)propane-2-sulfinamide (2.0 g, 5.16 mmol, 52.4% yield). MS m/z=387.9 [M+H]+. Calculated for C16H22F5NO2S: 387.13.

Workup

  1. customhad been degassed
  2. customby bubbling nitrogen through the solution for 30 minutes
  3. customThe reaction was quenched with saturated NaHCO3
  4. extractionextracted with EtOAc
  5. washthe combined organic extracts were washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel using 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-692fc5c945d1432384d6bf2a3d6cf913
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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