Fmoc-N-Me-Val-N-Me-Tyr(Bzl)-NH2 → N-Me-Val-N-Me-Tyr-NH2

HRID 2085559Notes

Reaction equation

HRID 2085559 reaction equation
[N:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)([CH3:29])[C@H:2]([C:6]([N:8]([CH3:28])[C@H:9]([C:25]([NH2:27])=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].[H][H]>CO.C(OCC)(=O)C.[OH-].[Pd+2].[OH-].[C]>[NH:1]([CH3:29])[C@H:2]([C:6]([N:8]([CH3:28])[C@H:9]([C:25]([NH2:27])=[O:26])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 2

HCID 131723957Fmoc-N-Me-Val-N-Me-Tyr(Bzl)-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 131723959N-Me-Val-N-Me-Tyr-NH2Yield 55%

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Fmoc-N-Me-Val-N-Me-Tyr(Bzl)-NH2(802 mg, 1.29 mmol) was dissolved in a mixed solution of MeOH (6 ml) and ethyl acetate (6 ml), mixed with 20% palladium hydroxide-carbon (150 mg), followed by stirring in a hydrogen atmosphere at room temperature for 2 days. The 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 10:1) to give the titled compound (216 mg, 55%).

Workup

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

Sources & evidence

ORD record
ord-d038849dc5a04e7f85dac5d9b0a621e0
Source dataset
uspto-grants-2004_04
Patent number
US06720433B2

Reaction notes

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