Ethyl bromoacetate → HCID 178472986, compound

HRID 2225607Notes

Reaction equation

HRID 2225607 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:30])[CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26]C(=O)C)[CH:19]=2)[CH2:10][CH2:9]1.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(O)C>[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][CH3:25])=[C:20]([O:26][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:19]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178490193HCID 178490193, compound

Product 1

HCID 178472986HCID 178472986, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.07 g of potassium carbonate was added to a solution of 4.97 g of N-(trans-4-methylcyclohexyl)-3-acetoxy-4-methoxycinnamamide (Example 193) in 200 ml of ethanol. The solution was stirred for 20 minutes, while it was refluxed. Next, 2.0 ml of ethyl bromoacetate was slowly added dropwise to the solution .by means of a dropping funnel. Thereafter, the solution was stirred for 2 hours. After reaction, the solution was allowed to cool to room temperature. The crystal and the potassium carbonate, both precipitated from the reaction solution, were filtered out, and the solvent was removed in vacuo from the filtrate. The product obtained was recrystallized from methylene chloride/ether, yielding 1.46 g of N-(trans-4-methylcyclohexyl)-3-(ethoxycarbonylmethoxy)-4-methoxycinnamamide (a compound the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. temperaturewas refluxed
  2. custommeans of a dropping funnel
  3. stirringThereafter, the solution was stirred for 2 hours
  4. customAfter reaction
  5. customThe crystal and the potassium carbonate, both precipitated from the reaction solution
  6. filtrationwere filtered out
  7. customthe solvent was removed in vacuo from the filtrate
  8. customThe product obtained
  9. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-ecd489bc601246e89af46ea256a0a811
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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