1-(4-Nitrophenyl)-2-dimethylamino-1,3-propanediol → (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid

HRID 1419555Notes

Reaction equation

HRID 1419555 reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.[N+](C1C=CC(C(O)C(N(C)C)CO)=CC=1)([O-])=O>C(O)C>[F:1][CH:2]([F:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]([CH:14]([CH3:15])[CH3:16])[C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 44309071-(4-Nitrophenyl)-2-dimethylamino-1,3-propanediolHCID 131185654-(Difluoromethoxy)-alpha-(1-methylethyl)benzeneacetic acid

Product 1

HCID 13118566(S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acidYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 50 g of 2-(4-difluoromethoxyphenyl)-3-methylbutyric acid in 150 g of ethyl alcohol and to this solution is added 0.24 mole of resolving agent 1-(4-nitrophenyl)-2-dimethylamino-1,3-propanediol. Heat the solution with stirring under reflux for 1.5 hours, then cool, filter, and transfer the resulting solids to 73 g of 10% hydrochloric acid. Heat the mixture with stirring at 30° C. for 2 hours and then allow the mixture to cool to room temperature. The resulting mixture is extracted with benzene 2-3 times, and the solvent benzene is then removed by distillation to give 21.25 g (yield: 42.5%) of (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid.

Workup

  1. additionto this solution is added 0.24 mole
  2. temperatureHeat the solution
  3. temperatureunder reflux for 1.5 hours
  4. temperaturecool
  5. filtrationfilter
  6. temperatureHeat the mixture
  7. stirringwith stirring at 30° C. for 2 hours
  8. extractionThe resulting mixture is extracted with benzene 2-3 times
  9. customthe solvent benzene is then removed by distillation

Sources & evidence

ORD record
ord-b56f1de1041d4de09fd075abf63786c8
Source dataset
uspto-grants-1999_03
Patent number
US05886207

Reaction notes

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