Sulfamic Acid → 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acid

HRID 2387325Notes

Reaction equation

HRID 2387325 reaction equation
C(#N)C.[CH3:4][C:5]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18])([CH3:14])[CH2:6][C@:7]1([C:10]([F:13])([F:12])[F:11])[CH2:9][O:8]1.Cl([O-])=[O:24].[Na+].S(=O)(=O)(O)N>[Cl-].[Na+].O>[CH3:14][C:5]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]([OH:24])=[O:18])([CH3:4])[CH2:6][C@:7]1([C:10]([F:12])([F:13])[F:11])[CH2:9][O:8]1

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 6342AcetonitrileHCID 23668197Sodium ChloriteHCID 580261572-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzaldehyde

Product 1

HCID 498213602-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred, ice-cooled, acetonitrile (250 mL) solution of 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzaldehyde (20 g, 73.5 mmol) was added a solution of sodium chlorite (7.4 g, 73.5 mmol in 100 mL water) followed immediately by a solution of sulfamic acid (7.13 g, 73.5 mmol in 100 mL water). After 30 minutes, the ice-cooled reaction mixture was treated with 500 mL of brine and extracted with three 300 mL portions of ethyl acetate. The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to give 2-[1,1-dimethyl-2-((R)-2-trifluoromethyloxiranyl)ethyl]benzoic acid as a colorless thick oil (18 g, 85%).

Workup

  1. temperatureTo a stirred, ice-cooled
  2. customreaction mixture
  3. extractionextracted with three 300 mL portions of ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-405bd9893fd24589ba48376106685b36
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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