HCID 69946805, compound → HCID 22898682, compound

HRID 1018519Notes

Reaction equation

HRID 1018519 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([CH3:17])[NH:14][C:15]=1[CH3:16])=[O:9]>CC(CC(C)C)=O.O=[Mn]=O>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=2)=[C:12]([C:18]([O:20][CH3:21])=[O:19])[C:13]([CH3:17])=[N:14][C:15]=1[CH3:16])=[O:9]

Participants

4

Reactant 1

HCID 69946805HCID 69946805, compound

Product 1

HCID 22898682HCID 22898682, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 10 g (0.026 mol) of 2,6-Dimethyl-4-(3-hydroxyphenyl) 1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester, obtained as indicated in A), and 2.6 g (0.030 mol) of MnO2 in 50 ml of methylisobutylketone, was refluxed with stirring for 14 hours. The remaining solid was eliminated by filtration, and the liquid was concentrated to dryness under reduced pressure. The residue obtained was dissolved in 15 ml of 15% aq. HC1, then, the solution was washed with ethyl acetate (10 ml), the pH was adjusted to 8 with 20% aq. K2CO3. Finally, the solution was extracted with CH2C12 (2×50 ml), the organic extracts were dried over anh Na2SO4, and concentrated to dryness at reduced pressure. The residue appeared as an oil, which crystallised in 2 ml of methanol, and was transformed into the hydrochloride by dissolution in ethanol (10 ml) and addition of HC1 saturated diethyl ether (20 ml). A yellow solid was obtained (mp 95-7° C., MeOH) with a yield of 64%.

Workup

  1. customobtained
  2. temperaturewas refluxed
  3. filtrationThe remaining solid was eliminated by filtration
  4. concentrationthe liquid was concentrated to dryness under reduced pressure
  5. customThe residue obtained
  6. dissolutionwas dissolved in 15 ml of 15% aq. HC1
  7. washthe solution was washed with ethyl acetate (10 ml)
  8. extractionFinally, the solution was extracted with CH2C12 (2×50 ml)
  9. dry with materialthe organic extracts were dried over anh Na2SO4
  10. concentrationconcentrated to dryness at reduced pressure
  11. customcrystallised in 2 ml of methanol
  12. dissolutionwas transformed into the hydrochloride by dissolution in ethanol (10 ml)
  13. additionaddition of HC1 saturated diethyl ether (20 ml)
  14. customA yellow solid was obtained (mp 95-7° C., MeOH) with a yield of 64%

Sources & evidence

ORD record
ord-8450291191bb4cf5b8de1ed76a9ef530
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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