L-Alanyl-L-proline → HCID 6321214, compound

HRID 1758852Notes

Reaction equation

HRID 1758852 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].O=[C:15]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].[H][H]>C(O)C.[Pd]>[CH2:19]([O:18][C:16]([CH:15]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:17])[CH3:20]

Participants

6

Reactant 3

HCID 83525L-Alanyl-L-prolineHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 6321214HCID 6321214, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.814 g of L-alanyl-L-proline, 0.206 g of ethyl 2-oxo-4-phenylbutyrate, and 1.6 g of molecular sieves in 10 ml ethanol is hydrogenated at room temperature under 40 pounds pressure with 0.1 g of 10% Pd on carbon as catalyst. After uptake of hydrogen ceases the crude product obtained by filtration and concentration is absorbed on ion exchange resin, (Dowex 50, H+) and eluted with 2% pyridine in water to yield 0.224 g of N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline. HPLC indicates a 55:45 isomer ratio.

Workup

  1. customobtained by filtration and concentration
  2. customis absorbed on ion exchange resin, (Dowex 50, H+)
  3. washeluted with 2% pyridine in water

Sources & evidence

ORD record
ord-0d7f5d3a05a646bf80659b296ce95570
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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