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N-Benzyloxycarbonyl-L-leucine-N-methylamide → (2S)-2-amino-N,4-dimethylpentanamide

HRID 535933
Notes
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Reaction equation

HRID 535933 reaction equation
[CH3:1][NH:2][C:3](=[O:20])[C@H:4]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH:5]C(OCC1C=CC=CC=1)=O.[H][H]>[Pd].CO>[CH3:1][NH:2][C:3](=[O:20])[C@H:4]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH2:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14888798N-Benzyloxycarbonyl-L-leucine-N-methylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 11672684(2S)-2-amino-N,4-dimethylpentanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 20A (1.20 g, 4.31 mmol) and 10% palladium on carbon (300 mg) in MeOH (30 mL) was hydrogenated with a Parr shaker under 55 psi of hydrogen gas for 3 h. After filtration through celite, the filtrate was evaporated and azeotroped with EtOAc to give the desired intermediate 20B as white solid (quant. yield). LCMS (+ESI) m/z 145.1 [M+H]+.

Workup

  1. filtrationAfter filtration through celite
  2. customthe filtrate was evaporated
  3. customazeotroped with EtOAc

Sources & evidence

ORD record
ord-86e15f1ba4b747c597ba0464a36c3b9b
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes