Sodium Bicarbonate → HCID 86732189, compound

HRID 930367Notes

Reaction equation

HRID 930367 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:19][S@@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH2:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11])[C:5]([F:8])=[N:6][CH:7]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:19][S@@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH2:12][C@H:13]([OH:18])[C:14]([F:15])([F:17])[F:16])[CH2:10][F:11])[C:5]([F:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86732188HCID 86732188, compound

Product 1

HCID 86732189HCID 86732189, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-N-((S)-2-(5-bromo-2-fluoropyridin-3-yl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (6.32 g, 14.01 mmol) was dissolved in anhydrous methanol 75 mL and the solution was cooled in an ice bath. Sodium tetrahydroborate (0.795 g, 21.01 mmol) was added portionwise as solid. After stirring in the ice bath for 10 min, the reaction was worked up with saturated sodium bicarbonate and extracted with EtOAc three times. The combined organic layers were washed with brine and dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography using a gradient of 15-50% EtOAc/hexane to give (R)-N-((2S,4S)-2-(5-bromo-2-fluoropyridin-3-yl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (12e, 3.68 g, 58% yield). MS m/z=454.9 [M+H]+. Calculated for C14H18BrF5N2O2S: 453.3; and (R)-N-((2S,4R)-2-(5-bromo-2-fluoropyridin-3-yl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (1.5 g, 24% yield). MS m/z=454.9 [M+H]+. Calculated for C14H18BrF5N2O2S: 453.3.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-2e04d8af50b04398aab71105f312fcf0
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

Loading…