Boc-Gly-Gly-Ala-Pro-OBzl → Boc-Gly-Gly-Ala-Pro-OH

HRID 440232Notes

Reaction equation

HRID 440232 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:28][CH2:27][CH2:26][C@H:15]1[C:16]([O:18]CC1C=CC=CC=1)=[O:17])=[O:13])[CH3:11])=[O:8])=[O:4]>C(O)(=O)C.[Pd]>[NH:1]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:28][CH2:27][CH2:26][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH3:11])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 131719402Boc-Gly-Gly-Ala-Pro-OBzl

Product 1

HCID 53321812Boc-Gly-Gly-Ala-Pro-OH

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Boc-Gly-Gly-Ala-Pro-OBzl (30.0 g, 0.061 mole) was dissolved in glacial acetic acid (300 mL) and 3.0 g of 10% Palladium on activated charcoal was added. This mixture was hydrogenated at 40 psi for 6 h. The reaction mixture was faltered through celite and the solvent was removed in vacuum. The resulting residue was triturated with ether, filtered, washed with ether, and dried to obtain Boc-Gly-Gly-Ala-Pro-OH.

Workup

  1. customthe solvent was removed in vacuum
  2. customThe resulting residue was triturated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-be2b1dd31a284fe687fe460f3d8def13
Source dataset
uspto-grants-1996_05
Patent number
US05519004

Reaction notes

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