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

HRID 1155082Notes

Reaction equation

HRID 1155082 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]>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

4

Reactant 1

HCID 541541681-[(Benzyloxy)carbonyl]-5-oxo-L-prolyl-D-leucyl-L-prolinamide

Product 1

HCID 133125015-Oxo-L-prolyl-D-leucyl-L-prolinamideYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.78 g (8 mmoles) of Z-Glp-D-Leu-Pro-NH2 are dissolved in 150 ml of methanol, 0.8 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is evaporated, and the residue is triturated with ether. The resulting 2.5 g of amorphous crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 2.35 g (87%) of Glp-D-Leu-Pro-NH2 are obtained; Rf4 =0.48, [α]D25 =-83.3° (c=1%, in acetic acid).

Workup

  1. customhydrogen is bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is triturated with ether
  5. dissolutionThe resulting 2.5 g of amorphous crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-367cb3d03ed7428db64c68f6d4166856
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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