Boc-Ala-Gly-Gly-OBzl → Boc-ala-Gly-Gly-OH

HRID 1379603Notes

Reaction equation

HRID 1379603 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:9])=[O:5])[CH3:3]>C(O)C.[Pd]>[NH:1]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3]

Participants

4

Reactant 1

HCID 131720212Boc-Ala-Gly-Gly-OBzl

Product 1

HCID 7020897Boc-ala-Gly-Gly-OH

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.5 g (1.3 mmol) of Boc-Ala-Gly-Gly-OBzl (13) is dissolved in 25 ml of absolute ethanol (Aldrich) in a 50 ml round bottom flask equipped with a stirring bar, followed by addition of 50 mg of 10% Pd-C (Aldrich). The reaction mixture is stirred under hydrogen gas atmosphere using a balloon. After 24 h, the Pd-C catalyst is filtered out from the reaction mixture, and the filtrate is concentrated to furnish Boc-Ala-Gly-Gly-OH (14). 1H-NMR (CDCl3): 1.39 (3H, d, J=7.2 Hz), 1.43 (9H, s), 3.99-4.15 (5H, m), 5.03 (1H, br), 6.91-7.03 (2H, br). FABMS: 325 (M+Na).

Workup

  1. customequipped with a stirring bar
  2. filtrationthe Pd-C catalyst is filtered out from the reaction mixture
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-b2b1565f1401459b8a69642d22d5eace
Source dataset
uspto-grants-1997_09
Patent number
US05672584

Reaction notes

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