HCID 131713007, compound → HCID 131713006, compound

HRID 851728Notes

Reaction equation

HRID 851728 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]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[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]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 131713007HCID 131713007, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131713006HCID 131713006, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.0 g (4.51 mmoles) of Z-Glp-Leu-piperidine are dissolved in 40 ml of methanol, 0.4 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 residue is crystallized from ether. 1.12 g (81%) of Glp-Leu-piperidine are obtained; m.p.: 99°-100° C., Rf5 =0.71, [α]D25 =+30.4° (c=1%, in acetic acid). Analysis for amino acids: Glu=0.95 (1.0), Leu=1.00 (1.0).

Workup

  1. customis bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-fae149c3fff8478497efeb3e63882574
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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