Z-Glu(OtBu)-Val-Val-Pro-OBzl → H-Glu(OtBu)-Val-Val-Pro-OH

HRID 481261Notes

Reaction equation

HRID 481261 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:26]([N:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32]CC1C=CC=CC=1)=[O:31])=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:26]([N:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([OH:32])=[O:31])=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]

Participants

4

Reactant 1

HCID 131724226Z-Glu(OtBu)-Val-Val-Pro-OBzl

Product 1

HCID 131724225H-Glu(OtBu)-Val-Val-Pro-OH

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

H-Glu(OtBu)-Val-Val-Pro-OH was prepared by dissolving Z-Glu(OtBu)-Val-Val-Pro-OBzl (2.90 g, 3.89 mmol) in 100 mL methanol containing 1% acetic acid. Pearlman's catalyst, Pd(OH)2, (100 mg) was added and the flask was placed on the Parr hydrogenation apparatus with an initial H2 pressure of 34 psi. After three hours, the catalyst was removed by filtration through a celite pad and the filtrate was evaporated in vacuo to yield a yellow oil (1.30 g, 2.61 mmol, 67%). ESI/MS calculated for C24H42N4O7+H: 499.3 Found: 499.4.

Workup

  1. customthe catalyst was removed by filtration through a celite pad
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-61e956897cb44c5193026a1d28a61bc5
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

Loading…