HCID 131712539, compound → 5-Oxo-L-prolyl-3-cyclohexyl-L-alanyl-L-prolinamide

HRID 1155079Notes

Reaction equation

HRID 1155079 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:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:8]>C(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:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:8]

Participants

4

Reactant 1

HCID 131712539HCID 131712539, compound

Product 1

HCID 133125195-Oxo-L-prolyl-3-cyclohexyl-L-alanyl-L-prolinamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.07 g (6 mmoles) of Z-Glp-Cha-Pro-NH2 are dissolved in 60 ml of ethanol, 0.6 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for 2 hours. The catalyst is filtered off, the filtrate is evaporated, and the residue is triturated with ether. 2.15 g (95%) of Glp-Cha-Pro-NH2 are obtained as an amorphous solid; Rf4 =0.50, [α]D25 =-70.9° (c=1%, in acetic acid).

Workup

  1. customhydrogen is bubbled through the mixture for 2 hours
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-ed1f478d2ea64d10b27463b19eefcbea
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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