Methyl 6-chloro-5-nitronicotinate → (S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(isopropyl)amino)-5-nitronicotinate

HRID 69605

反応式

HRID 69605 の反応式
[CH:1]([NH:4][C@@H:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH3:3])[CH3:2].Cl[C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1>CCOC(C)=O>[CH2:9]([O:8][C:6](=[O:7])[C@@H:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:13]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1)[CH3:11])[CH3:10]

参加物

4

反応物 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 45086712(S)-ethyl 2-(isopropylamino)propanoate

生成物 1

HCID 58324420(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(isopropyl)amino)-5-nitronicotinate収率 42%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

(S)-ethyl 2-(isopropylamino)propanoate (2.83 g, 17.8 mmol) was added to methyl 6-chloro-5-nitronicotinate (1.72 g, 7.94 mmol) and the reaction mixture was stirred in a closed vial at 90° C. for 20 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, hexanes:ethyl acetate 4:1) to afford the title compound as yellow oil (1.12 g, 42%). 1H NMR (400 MHz, CHLOROFORM-d) δ (ppm): 1.18 (t, J=7.07 Hz, 3 H) 1.30 (d, J=6.32 Hz, 3 H) 1.36 (d, J=6.57 Hz, 3 H) 1.66 (d, J=6.82 Hz, 3 H) 3.48-3.62 (m, 1 H) 3.90 (s, 3 H) 4.03 (q, J=6.65 Hz, 1 H) 4.06-4.21 (m, 2 H) 8.54 (d, J=2.02 Hz, 1 H) 8.70 (d, J=2.02 Hz, 1 H); [M+H] calc'd for C15H21N3O6, 340; found, 340.

後処理

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

出典と根拠

ORDレコード
ord-a6f43525adcc4780807da5abb6d2dae9
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

関連ノート

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