HCID 131712542, compound → 5-Oxo-L-prolyl-L-leucyl-N-ethyl-L-prolinamide

HRID 1155083Notes

Reaction equation

HRID 1155083 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[CH2:26][CH2:25][CH2:24][C@H:18]1[C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]>O.[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[CH2:26][CH2:25][CH2:24][C@H:18]1[C:19]([NH:21][CH2:22][CH3:23])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]

Participants

4

Reactant 1

HCID 131712542HCID 131712542, compound

Product 1

HCID 133125255-Oxo-L-prolyl-L-leucyl-N-ethyl-L-prolinamideYield 66.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

1.07 g (2.14 mmoles) of Z-Glp-Leu-Pro-NH-Et are dissolved in 30 ml of water, 0.25 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for 1.5 hours. The catalyst is filtered off, the filtrate is evaporated, and the oily residue is dissolved in 20 ml of chloroform. The solution is dried over anhydrous sodium sulfate and then evaporated. A foam-like solid residue is obtained, which is triturated with a mixture of ether and hexane. 0.52 g (66%) of Glp-Leu-Pro-NH-Et are obtained; Rf4 =0.57, [α]D25 =-94.5° (c=1%, in acetic acid).

Workup

  1. customhydrogen is bubbled through the mixture for 1.5 hours
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. dissolutionthe oily residue is dissolved in 20 ml of chloroform
  5. dry with materialThe solution is dried over anhydrous sodium sulfate
  6. customevaporated
  7. customA foam-like solid residue is obtained
  8. customwhich is triturated with a mixture of ether and hexane

Sources & evidence

ORD record
ord-2fb553d0118f42819350df20afe14927
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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