Sodium Bicarbonate → HCID 58026179, compound

HRID 2387316Notes

Reaction equation

HRID 2387316 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]([CH3:20])([CH3:19])[CH2:11][C@:12]1([C:15]([F:18])([F:17])[F:16])[CH2:14][O:13]1.[C:21]([O-:24])(=[O:23])[CH3:22].[Na+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:19][C:10]([C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[CH2:2][O:24][C:21](=[O:23])[CH3:22])([CH3:20])[CH2:11][C@:12]1([C:15]([F:18])([F:17])[F:16])[CH2:14][O:13]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 58026177HCID 58026177, compound

Product 1

HCID 58026179HCID 58026179, compoundYield 255.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To 48 g (0.087 mol) of (R)-2-[2-(2-bromomethyl-4-fluorophenyl)-2-methylpropyl]-2-trifluoromethyloxirane in 1.3 L of DMF was added 36 g of sodium acetate (0.439 mol). The mixture was heated at 45° C. for 3 hours. The mixture was then cooled to room temperature and poured into 1.3 L of saturated aqueous sodium bicarbonate solution and extracted with 1800 mL of diethyl ether. The aqueous phase was filtered to remove a solid residue. The solid was washed with 1.3 L of diethyl ether. The organic phases were combined and washed with 2 L of brine and separated. The aqueous phase was extracted with 1800 mL of diethyl ether. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 0-5% ethyl acetate/hexanes to afford 74.2 g (83%) of acetic acid 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]-5-fluorobenzyl ester.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted with 1800 mL of diethyl ether
  3. filtrationThe aqueous phase was filtered
  4. customto remove a solid residue
  5. washThe solid was washed with 1.3 L of diethyl ether
  6. washwashed with 2 L of brine
  7. customseparated
  8. extractionThe aqueous phase was extracted with 1800 mL of diethyl ether
  9. dry with materialThe combined organic phases were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude mixture was chromatographed on silica gel using 0-5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d27c982109714f13b1b3f9f959725450
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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