N-(1-Ethoxycarbonylbutyl)-L-alanine benzyl ester → (2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

HRID 1651448Notes

Reaction equation

HRID 1651448 reaction equation
C([O:8][C:9](=[O:22])[C@H:10]([CH3:21])[NH:11][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:14][CH3:15])C1C=CC=CC=1>C(O)C.[Pd]>[CH2:19]([O:18][C:16]([C@@H:12]([NH:11][C@H:10]([C:9]([OH:22])=[O:8])[CH3:21])[CH2:13][CH2:14][CH3:15])=[O:17])[CH3:20]

Participants

4

Reactant 1

HCID 13773268N-(1-Ethoxycarbonylbutyl)-L-alanine benzyl ester

Product 1

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acidYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The S,S diastereoisomer benzylester from step (b) (6.2g) in ethanol (250ml) was hydrogenated at 3 atmospheres at room temperature for 30 minutes over 10% palladium on charcoal (0.6g). The catalyst was removed by filtration and the filtrate was evaporated to near dryness. The residue was slurried with diethyl ether and the white solid was filtered off and was dried to give the required product (3.8g) mp 153°-4°.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. filtrationthe white solid was filtered off
  4. customwas dried

Sources & evidence

ORD record
ord-c01576beaa3d49f4af515aab72091e63
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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