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

HRID 34420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34420
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-82123a1fcfd14738ae17362d2849cd8a
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761420

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