HCID 86732205, compound → HCID 86732204, compound

HRID 930377Notes

Reaction equation

HRID 930377 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]([NH:18][S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])([CH2:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]([NH:18][S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])([CH2:11][C@H:12]([OH:17])[C:13]([F:15])([F:14])[F:16])[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86732205HCID 86732205, compound

Product 1

HCID 86732204HCID 86732204, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Ru[p-cymeme](1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.119 g, 0.198 mmol) was added in one portion to a solution of (R)-N-((S)-2-(3-bromophenyl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (2.14 g, 4.95 mmol) in IPA (50 ml) (which had been degassed by bubbling nitrogen through the solution for 30 minutes prior to use) in a dry box at room temperature. After stirring overnight, the reaction was worked up with saturated sodium bicarbonate solution and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography using 20-100% EtOAc/hexane to give (R)-N-((2S,4S)-2-(3-bromophenyl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (1.83 g, 85% yield). MS m/z=435.8 [M+H]+. Calculated for C15H20BrF4NO2S: 434.3

Workup

  1. customhad been degassed
  2. customby bubbling nitrogen through the solution for 30 minutes
  3. customat room temperature
  4. extractionextracted with EtOAc three times
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-115daa3e6eb2498e9474b18f87f87a14
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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