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

HRID 851732Notes

Reaction equation

HRID 851732 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 541541661-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 133125035-Oxo-D-prolyl-L-leucyl-L-prolinamideYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.48 g (9.5 mmoles) of Z-D-Glp-Leu-Pro-NH2 are dissolved in 200 ml of methanol, 0.9 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 3.07 g of crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 2.90 g (90.5%) of D-Glp-Leu-Pro-NH2 are obtained; Rf5 =0.40, [α]D25 =-23.6° (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 3.07 g of crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-b36dae216ad14944bbc9132bd1409864
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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