Diisopropylethylamine → (S)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl ester

HRID 2175162Notes

Reaction equation

HRID 2175162 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.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])[CH3:13].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C@@H:17]([NH:21][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1)[CH2:18][CH2:19][CH3:20])[CH3:13]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 10773249Ethyl (3S)-3-aminohexanoate

Product 1

HCID 58497448(S)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl esterYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-3-nitro-6-picoline (500 mg, 2.99 mmol) in DMF (3 mL) were added the (S)-3-amino-hexanoic acid ethyl ester (554 mg, 3.48 mmol) and diisopropylethyl amine (DIPEA) (1.0 mL, 5.80 mmol). The reaction mixture was stirred at room temperature for 48 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. The resulting residue was purified by preparative TLC using hexane and ethyl acetate (4:1) as an eluent to afford 358 mg (42%) of the title compound as orange oil. LCMS, M++1, m/z: 296.65.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-efe654689a0d47b5a21c145335762ba2
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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