dibenzyl N-(N-butanoyl-L-valyl)-L-glutamate → N-(N-butanoyl-L-valyl)-L-glutamic acid

HRID 236499Notes

Reaction equation

HRID 236499 reaction equation
[C:1]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:15][CH2:16][C:17]([O:19]CC1C=CC=CC=1)=[O:18])=[O:12])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[C:1]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:27]([OH:29])=[O:28])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:12])[CH:8]([CH3:9])[CH3:10])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 54213157dibenzyl N-(N-butanoyl-L-valyl)-L-glutamate

Product 1

HCID 53954075N-(N-butanoyl-L-valyl)-L-glutamic acidYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of dibenzyl N-(N-butanoyl-L-valyl)-L-glutamate (613 mg) and palladium black (50 mg) in methanol (50 ml) was subjected to catalytic hydrogenation under atmospheric pressure. After the reaction mixture was filtered, the filtrate was concentrated under reduced pressure to give a residue which was recrystallized from petroleum ether to afford N-(N-butanoyl-L-valyl)-L-glutamic acid as crystals (343 mg).

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue which
  4. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-a41bdb0ceab343c782887b6261246620
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

Loading…