HCID 178451027, compound → HCID 178451025, compound

HRID 1197080Notes

Reaction equation

HRID 1197080 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:12]([NH:14][CH2:15][C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])=[O:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>CO.[Pd]>[NH2:1][C@@H:2]([C:12]([NH:14][CH2:15][C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])=[O:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9]

Participants

4

Reactant 1

HCID 178451027HCID 178451027, compound

Product 1

HCID 178451025HCID 178451025, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

After 5.5 g (7.6 mM) of Z-D-Glu(OtBu)-Gly-Arg-CHA was dissolved in 150 ml of MeOH, 1 g of palladium black was added to the solution followed by catalytic reduction at 30° C. for 5 hours. After the reaction, the catalyst was filtered off and the solvent was removed by distillation under reduced pressure. The residue was dissolved in 5.5 ml of 5% HCl-MeOH and 20 ml of MeOH. The solution was precipitated again in ether. The precipitates were taken out by filtration and dried and then purified through TOYOPEARL HW40F column using MeOH as a developing solvent to give 3.6 g (75.8%) of H-D-Glu(OtBu)-Gly-Arg-CHA.2HCl.

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst was filtered off
  3. customthe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in 5.5 ml of 5% HCl-MeOH
  5. customThe solution was precipitated again in ether
  6. filtrationThe precipitates were taken out by filtration
  7. customdried
  8. custompurified through TOYOPEARL HW40F column

Sources & evidence

ORD record
ord-9ff004cc03a74347a6902417168471ad
Source dataset
uspto-grants-1992_05
Patent number
US05116941

Reaction notes

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