(S)-2-(2-Nitro-phenylamino)-propionic acid tert-butyl ester → (S)-2-(2-Amino-phenylamino)-propionic acid tert-butyl ester

HRID 1747386Notes

Reaction equation

HRID 1747386 reaction equation
[C:1]([O:5][C:6](=[O:19])[C@@H:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:19])[C@@H:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 59497415(S)-2-(2-Nitro-phenylamino)-propionic acid tert-butyl ester

Product 1

HCID 59497437(S)-2-(2-Amino-phenylamino)-propionic acid tert-butyl esterYield 105.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-2-(2-Nitro-phenylamino)-propionic acid tert-butyl ester (1.6 g, 6.0 mmol) in MeOH (20 mL) was added a slurry of 10% Pd/C (dry) (300 mg). The reaction mixture was degasses using house vacuum aspirator and then saturated with H2 gas in balloon. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then filtered through a celite and the filtrate was concentrated to afford 1.5 g (100%) of the desired product as a dark brown oily residue. This product was used for the next reaction without purification.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d68b5dac7c4546a0829b4defaeedd18c
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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