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

HRID 1383743Notes

Reaction equation

HRID 1383743 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)-NH2

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (1.17 g) and 20% palladium hydroxide on carbon (0.24 g) in methanol (20 ml) was stirred at room temperature in a hydrogen atmosphere for 1 hour. The reaction mixture was filtered and washed with methanol. The solvent was distilled off under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 100:10:1) to give N-Me-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 609 mg (71%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. distillationThe solvent was distilled off under reduced pressure
  4. washeluting solvent

Sources & evidence

ORD record
ord-08eb33597ad1421e851e417f5c042a51
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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