(2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxypentanamide → (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide

HRID 1025300Notes

Reaction equation

HRID 1025300 reaction equation
[CH:1]1([NH:4][C:5](=[O:26])[C@@H:6]([OH:25])[C@@H:7]([N:10](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:8][CH3:9])[CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[NH2:10][C@@H:7]([CH2:8][CH3:9])[C@H:6]([OH:25])[C:5]([NH:4][CH:1]1[CH2:2][CH2:3]1)=[O:26]

Participants

4

Reactant 1

HCID 44594159(2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxypentanamide

Product 1

HCID 57872123(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(2S,3S)—N-Cyclopropyl-3-(dibenzylamino)-2-hydroxypentanamide (4.42 g, 12.5 mmol, Eq: 1.00) was hydrogenated with Pd(OH)2 (20% on carbon, 890 mg, 1.27 mmol, Eq: 0.101) in methanol (50 ml) under a hydrogen pressure of 3.5 bar for 4 h. The catalyst was removed by filtration, and residual solvent was removed under vacuum. The title compound was obtained as a light yellow solid (2.09 g, 96.8%, MS (m/e)=173.2 [M+H+]).

Workup

  1. customfor 4 h
  2. customThe catalyst was removed by filtration, and residual solvent
  3. customwas removed under vacuum

Sources & evidence

ORD record
ord-b15cc7124a8141229dfbf838cfe09e8d
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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