Hydrochloric Acid → HCID 178490514, compound

HRID 2225541Notes

Reaction equation

HRID 2225541 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:30])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]C(=O)C)=[C:20]([O:28][CH3:29])[CH:19]=2)[CH2:10][CH2:9]1.Cl>CO>[CH3:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([NH:14][C:15](=[O:30])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:28][CH3:29])[CH:19]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 178490552HCID 178490552, compound

Product 1

HCID 178490514HCID 178490514, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g of sodium carbonate was added to a solution of 2.8 g of N-(cis-4-methylcyclohexyl)-4-acetoxy-3-methoxycinnamamide (Example 104) in 100 ml of methanol. The solution was stirred for 2 hours at room temperature. After reaction, 2N hydrochloric acid was added to the reaction solution, acidifying the solution. The solution was extracted three times with 90 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The product obtained was recrystallized from ethyl acetate/hexane, yielding 2.2 g of N-(cis-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. additionwas added to the reaction solution
  2. extractionThe solution was extracted three times with 90 ml of ethyl acetate
  3. customThe organic layer obtained
  4. washwas washed twice with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThereafter, the solvent was removed in vacuo
  7. customThe product obtained
  8. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-545319dda0e544f98d0fadc73d67e915
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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