HCID 131712538, compound → HCID 13312515, compound

HRID 1155078Notes

Reaction equation

HRID 1155078 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:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH2:19])=[O:18])=[O:14])[CH2:11][CH3:12])=[O:8].[H][H]>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:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH2:19])=[O:18])=[O:14])[CH2:11][CH3:12])=[O:8]

Participants

5

Reactant 2

HCID 131712538HCID 131712538, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13312515HCID 13312515, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.67 g (6 mmoles) of Z-Glp-Abu-Pro-NH2 are dissolved in 100 ml of acetic acid. 0.5 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 triturated with ether. The resulting 1.82 g of amorphous crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 1.70 g (91%) of Glp-Abu-Pro-NH2 are obtained; Rf4 =0.24, [α]D25 =-102.5° (c=1%, in acetic acid).

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 triturated with ether
  5. dissolutionThe resulting 1.82 g of amorphous crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-3183972c08ed41e5b713a4a1cc80a490
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

Loading…