Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 → N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988231Notes

Reaction equation

HRID 1988231 reaction equation
[C:1]([N:11](C)[C@H:12]([C:16]([N:18]([CH3:35])[C@H:19]([C:32]([NH2:34])=[O:33])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])(OCC1C=CC=CC=1)=O.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH:11]([CH3:1])[C@H:12]([C:16]([N:18]([CH3:35])[C@H:19]([C:32]([NH2:34])=[O:33])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([CH3:31])([CH3:29])[CH3:30])[CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 131722751Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 99.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.98 g, 1.97 mmol) and 20% palladium hydroxide/carbon (0.10 g) in methanol (20 ml) was stirred at room temperature in a hydrogen atmosphere for 1.5 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: chloroform:methanol:aqueous ammonia=100:10:1) to give N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.71 g, 99%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3cfd255809224f93808a4c0d47515bb8
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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