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

HRID 2175167Notes

Reaction equation

HRID 2175167 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[C:16]([CH3:23])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([NH2:20])=[CH:18][CH:17]=[C:16]([CH3:23])[N:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 58497430(R)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497458(R)-3-(3-Amino-6-methyl-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl esterYield 107.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (R)-3-(6-methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester (398 mg, 1.21 mmol) in MeOH (10 mL) was added slurry of Pd/C (150 mg) in MeOH (2 mL). The reaction mixture was degassed using house vacuum. The flask was saturated with H2 and stirred under H2 balloon for 2 hours. When the reaction was completed, the mixture was filtered through a pad of celite and the filtrate was concentrated to afford 390 mg (100%) of the oily residue. The resulting residue was used for the next reaction without further purification. LCMS, M++1, m/z: 300.15.

Workup

  1. customThe reaction mixture was degassed
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-453a2e01c66845518c813aeb7bef1e1d
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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