Potassium Carbonate → HCID 90192611, compound

HRID 923510Notes

Reaction equation

HRID 923510 reaction equation
[CH3:1][C:2]1([CH3:20])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@:5]([CH3:19])([C:14]2[N:15]=[N:16][NH:17][N:18]=2)[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].[F:27][C:28]([F:36])(S(F)(=O)=O)C(O)=O.C(=O)([O-])O.[Na+]>C(#N)C>[F:27][CH:28]([F:36])[N:16]1[N:17]=[N:18][C:14]([C@:5]2([CH3:19])[CH2:4][O:3][C:2]([CH3:20])([CH3:1])[N:6]2[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])=[N:15]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 90192604HCID 90192604, compound

Product 1

HCID 90192611HCID 90192611, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under a nitrogen gas flow, to a mixture of 9.89 g of tert-butyl (4R)-2,2,4-trimethyl-4-(2H-tetrazol-5-yl)-1,3-oxazolidine-3-carboxylate, 11 g of potassium carbonate, and 200 ml of acetonitrile was added dropwise 7.5 ml of 2,2-difluoro-2-(fluorosulfonyl)acetic acid under ice-cooling, followed by warming to room temperature and stirring for 1 hour. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 7.59 g of tert-butyl (4R)-4-[2-(difluoromethyl)-2H-tetrazol-5-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was then evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a6364ea2fed446f4a0e10378c26fb785
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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