N-Benzyl 2-(Carbobenzyloxyamino)-3-Methoxypropionamide → 2-amino-N-benzyl-3-methoxypropanamide

HRID 1882740Notes

Reaction equation

HRID 1882740 reaction equation
[CH2:1]([NH:8][C:9](=[O:25])[CH:10]([NH:14]C(OCC1C=CC=CC=1)=O)[CH2:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([NH:8][C:9](=[O:25])[CH:10]([NH2:14])[CH2:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 23509063N-Benzyl 2-(Carbobenzyloxyamino)-3-Methoxypropionamide

Product 1

HCID 98371812-amino-N-benzyl-3-methoxypropanamideYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 12 (122.8 mg, 0.36 mmol) in methanol (2.0 mL) was added 10% Pd—C (11 mg) and the mixture stirred at room temperature in the presence of H2 gas for 75 min. Celite was added to the reaction mixture and the catalyst was removed by filtration. The clear filtrate was evaporated in vacuo to give pure 13 as a clear viscous oil (72 mg, 97%): Rf 0.30 (5% MeOH/CHCl3).

Workup

  1. additionCelite was added to the reaction mixture
  2. customthe catalyst was removed by filtration
  3. customThe clear filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7bf14b3a8725413cb290f5016c293b3a
Source dataset
uspto-grants-2004_07
Patent number
USRE038551E1

Reaction notes

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