1-[(Benzyloxy)carbonyl]-5-oxo-L-prolyl-L-leucyl-D-prolinamide → 5-Oxo-L-prolyl-L-leucyl-D-prolinamide

HRID 851715Notes

Reaction equation

HRID 851715 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@@H:18]1[C:19]([NH2:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[H][H]>CO.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@@H:18]1[C:19]([NH2:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]

Participants

5

Reactant 2

HCID 541541671-[(Benzyloxy)carbonyl]-5-oxo-L-prolyl-L-leucyl-D-prolinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 133125025-Oxo-L-prolyl-L-leucyl-D-prolinamideYield 79.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.5 g (3.25 mmoles) of Z-Glp-Leu-D-Pro-NH2 are dissolved in 70 ml of methanol, 0.3 g of a 10% palladium-on-carbon catalyst are added to the solution, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is evaporated, and the amorphous residue is triturated with ether. The resulting 0.94 g of crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 0.87 g (79%) of Glp-Leu-D-Pro-NH2 are obtained; Rf5 =0.47, [α]D25 =+8.4° (c=1%, in acetic acid).

Workup

  1. customis bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe amorphous residue is triturated with ether
  5. dissolutionThe resulting 0.94 g of crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-b21af25b3bb24e95bd2e5cb8268b6da7
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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