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

HRID 2087124Notes

Reaction equation

HRID 2087124 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
  3. customto yield a yellow oil (1.30 g, 2.61 mmol. 67%)

Sources & evidence

ORD record
ord-262cd1264f844523bd2829fad993681d
Source dataset
uspto-grants-2004_04
Patent number
US06727366B2

Reaction notes

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