Sodium ethoxide → HCID 67402847, compound

HRID 1186416Notes

Reaction equation

HRID 1186416 reaction equation
C1([C@H](NC(=O)[O:11][C@@H:12]([C:17]2[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:13]([F:16])([F:15])[F:14])C)C=CC=CC=1.[O-]CC.[Na+]>C(O)C>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C@H:12]([OH:11])[C:13]([F:15])([F:14])[F:16])=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86657936HCID 86657936, compound

Product 1

HCID 67402847HCID 67402847, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-2,2,2-Trifluoro-1-(6-methylpyridin-3-yl)ethyl(R)-1-phenylethylcarbamate (946 mg, 2.80 mmol) was dissolved in ethanol (14 mL). To this, sodium ethoxide (1.90 g, 28.0 mmol) was added and the mixture was heated to reflux for 2 hours. The reaction mixture was concentrated, a 5% aqueous acetic acid solution was added thereto, and extraction with ethyl acetate was performed, followed by washing with a saturated aqueous sodium bicarbonate solution and brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give Compound EAA (493 mg, yield: 92%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiona 5% aqueous acetic acid solution was added
  5. extractionextraction with ethyl acetate
  6. washby washing with a saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. customThe solvent was evaporated off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7)
  10. customto give Compound EAA (493 mg, yield: 92%)

Sources & evidence

ORD record
ord-ccb19df333ab46b98013197abada278a
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…