N-bromobutanimide → HCID 49765956、化合物

HRID 2203645ノート

反応式

HRID 2203645 の反応式
[CH3:1][O:2][CH:3]([O:24][CH3:25])[CH2:4][N:5]1[CH:10]=[CH:9][C:8](=[O:11])[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]1[C:20]([O:22][CH3:23])=[O:21].C1C(=O)N([Br:33])C(=O)C1>ClCCl>[CH3:25][O:24][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[CH:10]=[C:9]([Br:33])[C:8](=[O:11])[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]1[C:20]([O:22][CH3:23])=[O:21]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 58067201HCID 58067201、化合物

生成物 1

HCID 49765956HCID 49765956、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A 2 L flask equipped with a mechanic stirrer were charged with methyl 1-[2,2-bis(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 23 as obtained above and 500 mL of dichloromethane. To this flask was added NBS (30 g, 0.17 mole) portion-wise. The reaction was stirred at room temperature until its completion (monitored by TLC, ˜6 hours). The mixture was then diluted with dichloromethane and washed with NaHCO3 (ss). The organic phase was dried over Na2SO4 before evaporation of the solvents. The crude product was purified by column chromatography (silica gel, EtOH/DCM: 0-40%) to afford methyl 1-[2,2-bis(methyloxy)ethyl]-5-bromo-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 24 as a light brown solid (50 g, 60% over three steps). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.7 (s, 1H), 7.4 (m, 2H), 7.3 (d, J=7.9 Hz, 3H), 5.3 (s, 2H), 4.4 (s, 1H), 3.8 (d, J=4.8 Hz, 2H), 3.8 (s, 3H), 3.4 (s, 6H). LC-MS (M+H+): calcd 426. obsd 426.

後処理

  1. customA 2 L flask equipped with a mechanic stirrer
  2. washwashed with NaHCO3 (ss)
  3. dry with materialThe organic phase was dried over Na2SO4 before evaporation of the solvents
  4. customThe crude product was purified by column chromatography (silica gel, EtOH/DCM: 0-40%)

出典と根拠

ORDレコード
ord-054c91fd742c4fa8824d837564797d43
出典データセット
uspto-grants-2016_06
特許番号
US09365587B2

反応ノート

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