HCID 54324563, compound → HCID 22823316, compound

HRID 851720Notes

Reaction equation

HRID 851720 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:14]([NH:16][C@H:17]([C:22]([NH2:24])=[O:23])[C@H:18]([CH2:20][CH3:21])[CH3:19])=[O:15])[CH2:11][CH2:12][CH3:13])=[O:8]>C(O)(=O)C.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:14]([NH:16][C@H:17]([C:22]([NH2:24])=[O:23])[C@H:18]([CH2:20][CH3:21])[CH3:19])=[O:15])[CH2:11][CH2:12][CH3:13])=[O:8]

Participants

4

Reactant 1

HCID 54324563HCID 54324563, compound

Product 1

HCID 22823316HCID 22823316, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4.75 g (10 mmoles) of Z-Glp-Nva-Ile-NH2 are dissolved in 200 ml of acetic acid, 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. 3.34 g (98%) of Glp-Nva-Ile-NH2 are obtained; m.p.: 267°-270° C. (decomposition), Rf5 =0.61, [α]D25 =-50.2° (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

Sources & evidence

ORD record
ord-6a2db2e2a51c488eb71f71be783005f9
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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