HCID 20522501, compound → L-Phenylalanyl-L-valine

HRID 223097Notes

Reaction equation

HRID 223097 reaction equation
C[O:2][C:3]([CH:5]([N:9]1[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]([NH2:19])[C:10]1=[O:20])[CH:6]([CH3:8])[CH3:7])=[O:4]>C(O)C.[Pd]>[NH2:19][C@H:11]([C:10]([NH:9][C@H:5]([C:3]([OH:4])=[O:2])[CH:6]([CH3:8])[CH3:7])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 20522501HCID 20522501, compound

Product 1

HCID 7359122L-Phenylalanyl-L-valineYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

According to the same procedure as in Example 1, 1-(methoxycarbonyl-2-methylpropyl)-3-amino-4-phenylazetidin-2-one (458 mg.) was subjected to hydrogenolysis at 50° C. in ethanol (30 ml.) under a hydrogen pressure of one atmosphere in the presence of a 10% Pd-C (175 mg.). The reaction was completed in 12 hours. The same after-treatment as in Example 1 was followed to give methyl ester of phenylalanylvaline (376 mg., yield: 81.5%) which was an oil. The NMR and IR spectra were completely identical with those of the authentic sample obtained in Example 5.

Sources & evidence

ORD record
ord-491ecf2f12294709bb47c21228933d86
Source dataset
uspto-grants-1982_10
Patent number
US04352752

Reaction notes

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