Water → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-acetoxyethyl)phenoxy]ethoxycarbonyl)-1,4-dihydropyridine

HRID 34420노트

반응식

HRID 34420 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:21]([O:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][OH:35])=[CH:29][CH:28]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].N1C=CC=CC=1.[C:43](OC(=O)C)(=[O:45])[CH3:44].O>C(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:21]([O:23][CH2:24][CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][O:35][C:43](=[O:45])[CH3:44])=[CH:31][CH:32]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 142087992,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethyl)phenoxy]ethoxycarbonyl)-1,4-dihydropyridine

생성물 1

HCID 142088002,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-acetoxyethyl)phenoxy]ethoxycarbonyl)-1,4-dihydropyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethyl)phenoxy]ethoxycarbonyl)-1,4-dihydropyridine (1.25 g, 2.52 mmoles) in CH2Cl2 (15 mL) cooled to 0° C., were added pyridine (0.25 mL, 3.10 mmoles) and acetic anhydride (0.85 mL, 9.0 mmoles). The reaction mixture was left at room temperature for 24 hours. Water (20 mL) was then added to extract the pyridine. The organic layer was dried over anhydrous Na2SO4. After evaporation of the solvent, the crude product (1.5 g) was purified by flash chromatography (solvent=93:7 CH2Cl2 :acetone) to yield 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-acetoxyethyl)phenoxy]ethoxycarbonyl)-1,4-dihydropyridine, mp=110° C. NMR (CDCl3) δppm: 8.2(m, 9H); 5.15(s, 1H); 4.5-3.9(m, 6H); 3.63(s, 3H); 2.87(t, 2H); 2.37(s, 6H); 2.07(s, 3H).

후처리

  1. extractionto extract the pyridine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customAfter evaporation of the solvent
  4. customthe crude product (1.5 g) was purified by flash chromatography (solvent=93:7 CH2Cl2 :acetone)

출처 및 근거

ORD 기록
ord-82123a1fcfd14738ae17362d2849cd8a
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761420

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