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

HRID 1988244Notes

Reaction equation

HRID 1988244 reaction equation
[C:1]([N:11](C)[C@H:12]([C:16]([N:18]([CH3:37])[C@H:19]([C:32]([NH:34][O:35][CH3:36])=[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]([CH3:37])[C@H:19]([C:32]([NH:34][O:35][CH3:36])=[O:33])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([CH3:29])([CH3:30])[CH3:31])[CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 131727511Z-N-Me-Val-N-Me-Tyr(3-tBu)-NHOMeHCID 178418361HCID 178418361, compound

Product 1

HCID 131727513N-Me-Val-N-Me-Tyr(3-tBu)-NHOMeYield 99.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of Z-N-Me-Val-N-Me-Tyr(3-tBu)-NHOMe (1.23 g, 2.33 mmol) in MeOH (20 ml), palladium hydroxide/carbon (350 mg) was added and stirred in a hydrogen atmosphere for 1 hour. Insoluble matters were removed by filtration with Celite and the filtrate was concentrated under reduced pressure to give crude N-Me-Val-N-Me-Tyr(3-tBu)-NHOMe (0.91 g).

Workup

  1. customInsoluble matters were removed by filtration with Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-538f2e9b2b6d49fa80ef73c978b7d728
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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