Hydrochloric Acid → HCID 86732202, compound

HRID 930376Notes

Reaction equation

HRID 930376 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:21][S@@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])([CH2:11]/[C:12](=N/N(C)C)/[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1.Cl.C(=O)(O)[O-:30].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:21][S@@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])([CH2:11][C:12](=[O:30])[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90373179HCID 90373179, compound

Product 1

HCID 86732202HCID 86732202, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-N-((Z)-2-(3-bromophenyl)-4-(2,2-dimethylhydrazono)-1,5,5,5-tetrafluoropentan-2-yl)-2-methylpropane-2-sulfinamide (1.47 g, 3.10 mmol) was dissolved in THF 16 mL and 2N hydrochloric acid (1.549 ml, 3.10 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture 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 a gradient of 15-50% EtOAc/hexane to give (R)-N-(2-(3-bromophenyl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (1.13 g, 84% yield). MS m/z=433.9 [M+H]+. Calculated for C15H18BrF4NO2S: 432.3

Workup

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

Sources & evidence

ORD record
ord-7bd5f386328f46d6a5b42a6bda03b4bb
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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