HCID 54024429, compound → HCID 13312505, compound

HRID 1155074Notes

Reaction equation

HRID 1155074 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][CH2:12][CH2:13][CH3:14])=[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][CH2:12][CH2:13][CH3:14])=[O:8]

Participants

5

Reactant 2

HCID 54024429HCID 54024429, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13312505HCID 13312505, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.16 g (2.46 mmoles) of Z-Glp-Nle-Pro-NH2 are dissolved in 25 ml of methanol. 0.2 g of a 10% palladium-on-carbon catalyst is added to the solution, and hydrogen is bubbled through the mixture for 30 minutes. The catalyst is filtered off, the filtrate is evaporated, and the solid, amorphous residue is triturated with ether. The resulting 0.72 g of crude product is dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 0.66 g (79.5%) of Glp-Nle-Pro-NH2 are obtained: Rf4 =0.43, [α]D25 =-77.1° (c=1%, in acetic acid). Amino acid analysis: Glu: 0.96 (1.0), Nle: 1.00 (1.0), Pro: 1.00 (1.0).

Workup

  1. customis bubbled through the mixture for 30 minutes
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe solid, amorphous residue is triturated with ether
  5. dissolutionThe resulting 0.72 g of crude product is dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-cf4f35fe7cd34fdfb841a602d4d051f5
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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