(R)-3-(6-Cyano-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester → (R)-3-(3-Amino-6-cyano-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175194Notes

Reaction equation

HRID 2175194 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[C:16]([C:23]#[N:24])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][CH:17]=[C:16]([C:23]#[N:24])[N:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 58497401(R)-3-(6-Cyano-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497449(R)-3-(3-Amino-6-cyano-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-3-(6-cyano-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester (0.70 g, 2.06 mmol) in EtOH (20 mL) was added Pd/C (140 mg). The reaction mixture was de-gassed using house vacuum and saturated with H2. The reaction mixture was stirred at room temperature for 2 hours. The mixture was filtered through a pad of celite and the filtrate was concentrated to afford 0.60 g (94%) of the title compound, which was used for the next reaction without further purification.

Workup

  1. customThe reaction mixture was de-gassed
  2. filtrationThe mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-37fd6a6fb476436ea43032845e2af85a
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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