Sodium Hydroxide → (R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid

HRID 221424Notes

Reaction equation

HRID 221424 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C@H:6]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16])C.[OH-].[Na+]>CO.O>[C:21]([O:20][C:18]([NH:17][C@H:6]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16])[CH2:5][C:4]([OH:25])=[O:3])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57518395HCID 57518395, compound

Product 1

HCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(R)-3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid ethyl ester 1e (10 g, 27.7 mmol) and sodium hydroxide (3.32 g, 83.1 mmol) were dissolved in the solvent mixture of 100 mL of methanol and 50 mL of water under stirring. The reaction mixture was reacted at 40-45° C. for 1-1.5 hours, then part of the solution was evaporated under reduced pressure. The residue was added with some water, then pH was adjusted to 2-3 with 1 N hydrochloric acid in an ice-water bath. The mixture was extracted with ethyl acetate (200 mL×3), and the combined organic phase was washed with 200 mL of saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, and then recrystallized from ethyl acetate/n-hexane to obtain the title compound (R)-3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid if (9.2 g) as a white solid, which was directly used in the next step.

Workup

  1. customThe reaction mixture was reacted at 40-45° C. for 1-1.5 hours
  2. custompart of the solution was evaporated under reduced pressure
  3. additionThe residue was added with some water
  4. custompH was adjusted to 2-3 with 1 N hydrochloric acid in an ice-water bath
  5. extractionThe mixture was extracted with ethyl acetate (200 mL×3)
  6. washthe combined organic phase was washed with 200 mL of saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-47ebe16bd5124e839b855ec6a23c0c4a
Source dataset
uspto-grants-2012_06
Patent number
US08207161B2

Reaction notes

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