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

HRID 260250Notes

Reaction equation

HRID 260250 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 filtered through celite and the solvent was removed in vacuum. The resulting residue was triturated with ether, faltered, washed with ether, and dried to obtain Boc-Gly-Gly-Ala-Pro-OH.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed in vacuum
  3. customThe resulting residue was triturated with ether
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-ba75f07f17344df7bdaa8bafc0bdb6dc
Source dataset
uspto-grants-1996_06
Patent number
US05527610

Reaction notes

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