Hydrochloric Acid → HCID 86732188, compound

HRID 930366Notes

Reaction equation

HRID 930366 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:22][S@@:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])([CH2:12]/[C:13](=N/N(C)C)/[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11])[C:5]([F:8])=[N:6][CH:7]=1.Cl.C([O-])(O)=[O:31].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:22][S@@:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])([CH2:12][C:13](=[O:31])[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11])[C:5]([F:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90372982HCID 90372982, compound

Product 1

HCID 86732188HCID 86732188, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-N-((S,Z)-2-(5-bromo-2-fluoropyridin-3-yl)-4-(2,2-dimethylhydrazono)-1,5,5,5-tetrafluoropentan-2-yl)-2-methylpropane-2-sulfinamide (0.510 g, 1.034 mmol) was dissolved in THF 5 mL. Hydrochloric acid 1N solution (1.034 ml, 1.034 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight and worked up with saturated aqueous NaHCO3 and extracted with EtOAc three times. The combined organic layers were washed with brine, dried on 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-((S)-2-(5-bromo-2-fluoropyridin-3-yl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (0.356 g, 0.789 mmol, 76% yield). MS m/z=490.9 [M+CH3CN]+. Calculated for C14H16BrF5N2O2S: 451.250.

Workup

  1. extractionextracted with EtOAc three times
  2. washThe combined organic layers were washed with brine
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-e4740473b4724485a1ef85ba947a7655
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

Loading…