Water → 2,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-hydroxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

HRID 34419Notes

Reaction equation

HRID 34419 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:43])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][O:36]C3CCCCO3)=[CH:30][CH:29]=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].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl.O>CO>[CH3:1][C:2]1[NH:3][C:4]([CH3:43])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][OH:36])=[CH:32][CH:33]=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 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 142087862,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

Product 1

HCID 141785532,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-hydroxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridineYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (4.0 g, 6.7 mmoles) in methanol (50 mL) was added a catalytic amount of 4-toluenesulfonic acid. After 24 hours, 200 mL of CH2Cl2 and 100 mL of H2O were added. The organic extracts were dried over anhydrous Na2SO4 and the solvent evaporated. The residue (3.5 g) was purified by flash chromatography (80:20 CH2Cl2 :acetone). Evaporation of the pure fractions gave 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-hydroxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine (2.4 g, mp <50° C.). NMR (CDCl3)δppm: 8.1-6.5(m, 9H); 5.02(s, 1H); 4.13(t, 2H); 4.0-3.4(m, 7H); 2.68(t, 2H); 2.47(s, 1H); 2.27(s, 6 H); 2.3-1.8(m, 2H).

Workup

  1. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  2. customthe solvent evaporated
  3. customThe residue (3.5 g) was purified by flash chromatography (80:20 CH2Cl2 :acetone)
  4. customEvaporation of the pure fractions

Sources & evidence

ORD record
ord-c8dcce0e3cc94a958112dffd2a4d569f
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Reaction notes

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