Sodium Hydroxide → (3R)-N-[(Allyloxy)carbonyl]-4,4,4-trifluorovaline

HRID 626425Notes

Reaction equation

HRID 626425 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:15]([O:17]CC)=[O:16])[C@H:9]([C:11]([F:14])([F:13])[F:12])[CH3:10])=[O:6])[CH:2]=[CH2:3].[OH-].[Na+]>C1COCC1.C(O)C.O>[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:15]([OH:17])=[O:16])[C@H:9]([C:11]([F:13])([F:14])[F:12])[CH3:10])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 131735216Ethyl (3R)-N-[(allyloxy)carbonyl]-4,4,4-trifluorovalinate

Product 1

HCID 118106697(3R)-N-[(Allyloxy)carbonyl]-4,4,4-trifluorovaline

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.50 g (22.9 mmol) of ethyl (3R)—N-[(allyloxy)carbonyl]-4,4,4-trifluorovalinate (diastereomer mixture) were dissolved in a mixture of in each case 28 ml of THF, ethanol and water, and 13.77 g (344 mmol) of sodium hydroxide were added at 0° C. Ice-cooling was removed and the reaction mixture was stirred at RT overnight. The mixture was then added to water, acidified with semiconcentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. This gave 4.39 g of the target product which was not purified any further (75% of theory, diastereomer ratio about 2.5:1).

Workup

  1. additionwere added at 0° C
  2. temperatureIce-cooling
  3. customwas removed
  4. additionThe mixture was then added to water
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with sat. sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThis gave 4.39 g of the target product which was not purified any further (75% of theory, diastereomer ratio about 2.5:1)

Sources & evidence

ORD record
ord-51db4e2e5eaf43d69027249f0fe6e681
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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