Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me → N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me

HRID 1988241Notes

Reaction equation

HRID 1988241 reaction equation
[C:1]([N:11](C)[C@H:12]([C:16]([N:18]([CH3:39])[C@H:19]([C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O: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]([CH3:39])[C@H:19]([C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O: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]([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 131727506Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2MeHCID 178418361HCID 178418361, compound

Product 1

HCID 131727508N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2MeYield 100.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me (0.65 g, 1.13 mmol) and 20% palladium hydroxide/carbon (0.09 g) in methanol (10 ml) was stirred at room temperature for 2.5 hours in a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was evaporated to remove the solvent under reduced pressure, giving crude N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me (0.50 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-ddfcd71dfe69498085251f916009fb6f
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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