Ethanol → HCID 49864481, compound

HRID 614767Notes

Reaction equation

HRID 614767 reaction equation
C([O:8][C@H:9]([CH3:37])[C@@H:10]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[NH2:11])C1C=CC=CC=1.C(O)C>[Pd].C(O)(=O)C>[NH2:11][C@H:10]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[C@@H:9]([CH3:37])[OH:8]

Participants

5

Reactant 2

HCID 702EthanolHCID 54510168HCID 54510168, compound

Product 1

HCID 49864481HCID 49864481, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

One gram of benzyl O-benzylthreonylvalylleucinate hydrochloride is neutralized to provide benzyl O-benzylthreonylvalylleucinate. A hydrogenolysis mixture is prepared containing the benzyl O-benzylthreonylvalylleucinate, 0.5 grams of 10 percent palladium on charcoal per 0.01 mole of the material to be hydrogenated, and absolute ethanol. To the mixture is added 1.1 mole equivalents of acetic acid based on the benzyl ester. The mixture is hydrogenated for 4 hours. The catalyst is removed by filtration and the solvents are removed in vacuo. The residue is washed with anhydrous ether and recrystallized from an ethanol/ether mixture to provide 544 milligrams of the free peptide, threonylvalylleucine (85% yield).

Workup

  1. customA hydrogenolysis mixture is prepared
  2. customThe catalyst is removed by filtration
  3. customthe solvents are removed in vacuo
  4. washThe residue is washed with anhydrous ether
  5. customrecrystallized from an ethanol/ether mixture

Sources & evidence

ORD record
ord-5ec593c93e0844f7abd489ae64398b10
Source dataset
uspto-grants-1979_03
Patent number
US04146614

Reaction notes

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