Hydrochloric Acid → N-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methyl]-4-acetoxy-3-methoxycinnamamide

HRID 2225491Notes

Reaction equation

HRID 2225491 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](Cl)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].N[CH2:19][C:20]12[CH2:27][CH2:26][C:23]([CH3:28])([CH2:24][CH2:25]1)[C:22](=[O:29])[O:21]2.Cl.[N:31]1C=CC=CC=1>>[CH3:19][C:20]12[CH2:27][CH2:26][C:23]([CH2:28][NH:31][C:11](=[O:12])[CH:10]=[CH:9][C:8]3[CH:14]=[CH:15][C:5]([O:4][C:1](=[O:3])[CH3:2])=[C:6]([O:16][CH3:17])[CH:7]=3)([CH2:24][CH2:25]1)[C:22](=[O:29])[O:21]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 190047031-Aminomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-oneHCID 544680224-Acetoxy-3-methoxycinnamoyl chloride

Product 1

HCID 54127133N-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methyl]-4-acetoxy-3-methoxycinnamamide

Procedure

0.65 g of 4-acetoxy-3-methoxycinnamoyl chloride was added to a solution of 0.44 g of 1-aminomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-one (Example 30) in 10 ml of pyridine. The resultant solution was stirred at room temperature for 16 hours. After reaction, 30 ml of 2N hydrochloric acid was added to the reaction solution. The resultant solution was extracted five times with 20 ml of ethyl acetate. The organic layer obtained was washed three times with 2N hydrochloric acid, twice with an aqueous sodium hydrogencarbonate solution and once with an aqueous sodium chloride solution, and then was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 0.58 g of N-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methyl]-4-acetoxy-3-methoxycinnamamide (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. additionwas added to the reaction solution
  2. extractionThe resultant solution was extracted five times with 20 ml of ethyl acetate
  3. customThe organic layer obtained
  4. washwas washed three times with 2N hydrochloric acid
  5. dry with materialtwice with an aqueous sodium hydrogencarbonate solution and once with an aqueous sodium chloride solution, and then was dried over magnesium sulfate
  6. customThereafter, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-f3313904063c498bb65904a82d81d772
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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