Ethyl Acetate → (S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(ethyl)amino)-5-nitronicotinate

HRID 1644916

Reaction equation

HRID 1644916 reaction equation
[CH2:1]([NH:3][C@@H:4]([CH3:9])[C:5]([O:7][CH3:8])=[O:6])[CH3:2].Cl[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1.[CH3:24]COC(C)=O>>[CH2:8]([O:7][C:5](=[O:6])[C@@H:4]([N:3]([CH2:1][CH3:2])[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)[CH3:9])[CH3:24]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 346961Methyl 6-chloro-5-nitronicotinateHCID 43230256(S)-N-ethylalanine methyl ester

Product 1

HCID 58324496(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(ethyl)amino)-5-nitronicotinateYield 66%

Conditions

Temperature
90 °C

Procedure

(S)-methyl 2-(ethylamino)propanoate (1.83 g, 14.0 mmol) was added to methyl 6-chloro-5-nitronicotinate (1.30 g, 6.00 mmol) and the reaction mixture was stirred in a closed vial at 90° C. for 1 h. It was cooled and diluted with EtOAc (25 mL). The resulting precipitate was filtered off, the filtrate was concentrated in vacuo and purified using flash column chromatography on silica gel (220 g SiO2, ethyl acetate in hexanes 0-50%) to afford the title compound as a yellow oil (1.23 g, 66%). [M+H] calc'd for C14H19N3O6, 326; found, 326.

Workup

  1. temperatureIt was cooled
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified

Sources & evidence

ORD record
ord-8a6b4aa0cb2244ddb577ed37fa235d9f
Source dataset
uspto-grants-2012_02
Patent number
US08124606B2

Linked notes

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