N-[2-(ethoxycarbonyl)ethyl]-N-t-butyloxycarbonyl-D-leucine benzyl ester → N-[2-(ethoxycarbonyl)ethyl]-N-t-butyloxycarbonyl-D-leucine

HRID 58035Notes

Reaction equation

HRID 58035 reaction equation
C([O:8][C:9](=[O:30])[C@@H:10]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:11]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[CH2:24]([O:23][C:21]([CH2:20][CH2:19][N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[C@@H:10]([C:9]([OH:30])=[O:8])[CH2:26][CH:27]([CH3:28])[CH3:29])=[O:22])[CH3:25]

Participants

5

Reactant 2

HCID 86700995N-[2-(ethoxycarbonyl)ethyl]-N-t-butyloxycarbonyl-D-leucine benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86700994N-[2-(ethoxycarbonyl)ethyl]-N-t-butyloxycarbonyl-D-leucineYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N-[2-(ethoxycarbonyl)ethyl]-N-t-butyloxycarbonyl-D-leucine benzyl ester (837 mg) was dissolved in methanol (25 ml), and 10% palladium-carbon (90 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 (612 mg, 93%), 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-66d78d45530d44e598c266f77f2a0b67
Source dataset
uspto-grants-2016_09
Patent number
US09434760B2

Reaction notes

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