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

HRID 2175166Notes

Reaction equation

HRID 2175166 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.Cl.[CH2:13]([O:15][C:16](=[O:26])[CH2:17][C@@H:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:26])[CH2:17][C@@H:18]([NH:25][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:14]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 2734508ethyl (3R)-3-amino-3-phenylpropanoate hydrochloride

Product 1

HCID 58497430(R)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl esterYield 104.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-3-nitro-6-picoline (200 mg, 1.16 mmol) in DMF (3 mL) were added (R)-3-amino-3-phenylpropanoic acid ethyl ester hydrochloride (319 mg, 1.39 mmol) and DIPEA (0.5 mL, 2.90 mmol). The reaction mixture was stirred at 70° C. for 12 hours. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated to afford 398 mg (100%) of the title compound as orange oil. The resulting residue was used for the next reaction without further purification. LCMS, M++1, m/z: 330.29.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3b7af614c1f34a50a70beb1352e3744e
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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