Ethyl bromoacetate → HCID 178472971, compound

HRID 2225608Notes

Reaction equation

HRID 2225608 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:27])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=2)[CH2:10][CH2:9]1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(O)C>[CH3:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([NH:14][C:15](=[O:27])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:20]([O:25][CH3:26])[CH:19]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178490514HCID 178490514, compound

Product 1

HCID 178472971HCID 178472971, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.03 g of potassium carbonate was added to a solution of 2.15 g of N-(cis-4-methylcyclohexyl)-4-hydroxy -3-methoxycinnamamide (Example 105) in 200 ml of ethanol. The solution was stirred for 20 minutes, while it was refluxed. Next, 8.0 ml of ethyl bromoacetate was slowly added dropwise to the solution by means of a dropping funnel. Thereafter, the solution was stirred for 4 hours. After reaction, the potassium carbonate was filtered from the reaction solution, and the solvent was removed in vacuo from the filtrate. The product obtained was recrystallized from methylene chloride/ether, yielding 2.12 g of N-(cis-4-methylcyclohexyl) -4-(ethoxycarbonylmethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. temperaturewas refluxed
  2. stirringThereafter, the solution was stirred for 4 hours
  3. customAfter reaction
  4. filtrationthe potassium carbonate was filtered from the reaction solution
  5. customthe solvent was removed in vacuo from the filtrate
  6. customThe product obtained
  7. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-a7f416d11a064880bc1e5ea4fd4ab2db
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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