4-Benzoyl-2(S)-trifluoroacetamidobutyric acid → 5-Phenyl-2(S)-trifluoroacetamidopentanoic acid

HRID 346177Notes

Reaction equation

HRID 346177 reaction equation
[C:1]([CH2:9][CH2:10][C@H:11]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:12]([OH:14])=[O:13])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[OH-].[Pd+2].CCOC(C)=O.C(O)C>[C:2]1([CH2:1][CH2:9][CH2:10][C@H:11]([NH:15][C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[C:12]([OH:14])=[O:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 143908104-Benzoyl-2(S)-trifluoroacetamidobutyric acid

Product 1

HCID 143908125-Phenyl-2(S)-trifluoroacetamidopentanoic acidYield 84.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reduce the product of Step 1 (9.7 g) with Pearlman's catalyst (3.5 g) in EtOAc (75 ml) and ethanol (25 ml) at 50 psi H2 for 3 hours. Filter, concentrate and wash the resultant residue with 3:1 hexane:diethyl ether to give the title compound (7.8 g).

Workup

  1. customfor 3 hours
  2. filtrationFilter
  3. concentrationconcentrate
  4. washwash the resultant residue with 3:1 hexane

Sources & evidence

ORD record
ord-95fecd7a65584593a81b39cbfa371fbd
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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