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

HRID 1155077Notes

Reaction equation

HRID 1155077 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])[C@H:11]([CH2:13][CH3:14])[CH3:12])=[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])[C@H:11]([CH2:13][CH3:14])[CH3:12])=[O:8]

Participants

4

Reactant 1

HCID 544786341-[(Benzyloxy)carbonyl]-5-oxo-L-prolyl-L-isoleucyl-L-prolinamide

Product 1

HCID 228184335-Oxo-L-prolyl-L-isoleucyl-L-prolinamideYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.72 g (10 mmoles) of Z-Glp-Ile-Pro-NH2 are dissolved in 100 ml of methanol, 1 g of a 10% palladium-on-carbon catalyst is 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 3.22 g of amorphous crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 3.03 g (89%) of Glp-Ile-Pro-NH2 are obtained; Rf4 =0.45, [α]D25 =-100.7° (c=1%, in acetic acid). Amino acid analysis: Glu: 0.95 (1.0), Ile: 1.00 (1.0), Pro: 1.02 (1.0).

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 3.22 g of amorphous crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-eb735a843395459eabdaa84e5dde9bd2
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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