N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester → N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

HRID 1906628Notes

Reaction equation

HRID 1906628 reaction equation
C([O:8][C:9](=[O:27])[C@H:10]([CH3:26])[NH:11][CH:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>C(O)C.C(O)(=O)C.[Pd]>[CH2:24]([O:23][C:21]([CH:12]([NH:11][C@H:10]([C:9]([OH:27])=[O:8])[CH3:26])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:22])[CH3:25]

Participants

6

Reactant 2

HCID 13345971N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine BenzylesterHCID 178418361HCID 178418361, compound

Product 1

HCID 13044262N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester (4.2 g) is dissolved in 40 ml ethanol, to which is added 630 mg 10% Pd-C and a few drops of acetic acid. Hydrogenation occurs under a 30 psi hydrogen atmosphere at room temperature overnight. The resulting mixture is filtered through celite and dried under vacuum to remove the solvent, yielding a residue. The residue is partitioned between chloroform and aqueous 5% NaHCO3, separated, and the chloroform layer further washed with aqueous 5% NaHCO3. The aqueous layers are combined, acidified to pH 3.5 with dilute HCl, extracted with chloroform or ethylacetate several times, dried over MgSO4, and placed under vacuum to evaporate the solvent and yield 2.5 g of the diastereoisomeric product, a brown sticky solid [TLC (Silica gel; CHCl3 /MeOH/HOAC=9:1:0.5); Rf=0.4].

Workup

  1. filtrationThe resulting mixture is filtered through celite
  2. customdried under vacuum
  3. customto remove the solvent
  4. customyielding a residue
  5. customThe residue is partitioned between chloroform and aqueous 5% NaHCO3
  6. customseparated
  7. washthe chloroform layer further washed with aqueous 5% NaHCO3
  8. extractionextracted with chloroform or ethylacetate several times
  9. dry with materialdried over MgSO4
  10. customto evaporate the solvent and yield 2.5 g of the diastereoisomeric product

Sources & evidence

ORD record
ord-b0927fd42b5647caac7d9bc33a5eef9a
Source dataset
uspto-grants-1987_03
Patent number
US04652668

Reaction notes

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