Acetone → (4R)-4-((tert-Butoxycarbonyl)amino)-5-(4-(trifluoromethyl)phenyl)pentanoic acid

HRID 598882Notes

Reaction equation

HRID 598882 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C@H:8]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=1.CC(C)=[O:27]>[OH-].[Na+]>[C:17]([O:16][C:14]([NH:9][C@@H:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:24])([F:23])[F:1])=[CH:22][CH:21]=1)[CH2:12][CH2:11][C:10]([OH:13])=[O:27])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 180AcetoneHCID 57950685(R)-tert-Butyl 2-(4-(trifluoromethyl)benzyl)-5-oxopyrrolidine-1-carboxylate

Product 1

HCID 57950597(4R)-4-((tert-Butoxycarbonyl)amino)-5-(4-(trifluoromethyl)phenyl)pentanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(R)-tert-Butyl 2-(4-(trifluoromethyl)benzyl)-5-oxopyrrolidine-1-carboxylate (4.0 g, 12 mmol) was dissolved in 25 mL acetone and 40 mL of 1.0 M aqueous sodium hydroxide. The resulting mixture was stirred for 30 minutes. The acetone was removed and the mixture was acidified with 5.0 M HCl. The resulting solid was filtered and washed with water twice. The crude product was recrystallized from hexane/EtOAc solvent (10:1 ratio, total volume hexane: 100 mL). After the solution was cooled, the crystals slowly appeared and the solution was put in the freezer for 2 hours. Filtration of the solid afforded the desired compound as a white crystalline solid (3.9 g, 93%). MS (API-ES) m/z (%): 384.1 (100%, M++Na).

Workup

  1. customThe acetone was removed
  2. filtrationThe resulting solid was filtered
  3. washwashed with water twice
  4. customThe crude product was recrystallized from hexane/EtOAc solvent (10:1 ratio, total volume hexane: 100 mL)
  5. temperatureAfter the solution was cooled
  6. waitthe solution was put in the freezer for 2 hours
  7. filtrationFiltration of the solid

Sources & evidence

ORD record
ord-16e73c84d3ed4f488108fb6f9700f77f
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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