N-bromobutanimide → HCID 49765956, 화합물

HRID 594839노트

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HRID 594839 반응식
[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]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 58067201HCID 58067201, 화합물

생성물 1

HCID 49765956HCID 49765956, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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 chromatargraphy (silcal 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.

후처리

  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 chromatargraphy (silcal gel, EtOH/DCM: 0-40%)

출처 및 근거

ORD 기록
ord-9aa86f32358c415c814d650dc971b73f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242986B2

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