N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide → HCID 66666062, compound

HRID 81606Notes

Reaction equation

HRID 81606 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C:8]([NH:22]S(C(C)(C)C)=O)([C:10]([F:21])([F:20])[CH2:11][O:12][Si](C(C)(C)C)(C)C)[CH3:9])[CH:7]=1>CO.Cl>[NH2:22][C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:29])([CH3:9])[C:10]([F:20])([F:21])[CH2:11][OH:12]

Participants

4

Reactant 1

HCID 66666208N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 66666062HCID 66666062, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide (8.8 g, 17.08 mmol) in dry MeOH (60 mL), dry HCl gas was purged for 30 min at −22° C. Reaction mixture was concentrated under reduced pressure and basified with NH4OH solution under cooling. Product was extracted with dichloromethane, washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to furnish title compound as a color less thick liquid. Yield=4.4 g (88%).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. temperatureunder cooling
  4. extractionProduct was extracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1070da785b60416c95f11eb18cdfbf39
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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