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

HRID 34420Notes

Reaction equation

HRID 34420 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-82123a1fcfd14738ae17362d2849cd8a
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Reaction notes

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