N-(t-butyloxycarbonyl)methyl-N-t-butyloxycarbonyl-D-leucine benzyl ester → N-(t-butyloxycarbonyl)methyl-N-t-butyloxycarbonyl-D-leucine

HRID 58032Notes

Reaction equation

HRID 58032 reaction equation
C([O:8][C:9](=[O:31])[C@@H:10]([CH2:27][CH:28]([CH3:30])[CH3:29])[N:11]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:23]([O:22][C:20]([CH2:19][N:11]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[C@@H:10]([C:9]([OH:31])=[O:8])[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 86700985N-(t-butyloxycarbonyl)methyl-N-t-butyloxycarbonyl-D-leucine benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86700984N-(t-butyloxycarbonyl)methyl-N-t-butyloxycarbonyl-D-leucineYield 99.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N-(t-butyloxycarbonyl)methyl-N-t-butyloxycarbonyl-D-leucine benzyl ester (2.1 g) was dissolved in methanol (25 ml), and 10% palladium-carbon (210 mg) was added. The resulting mixture aerated with hydrogen was allowed to react at room temperature for 3 h, filtered and concentrated under reduced pressure to remove the solvent to give a colourless oil (1.66 g, 96%), which was directly used for the next reaction.

Workup

  1. customto react at room temperature for 3 h
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-f2c8c4aa22584e9eb0091ea75c82d0c9
Source dataset
uspto-grants-2016_09
Patent number
US09434760B2

Reaction notes

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