Methanol → HCID 178472972, compound

HRID 2225591Notes

Reaction equation

HRID 2225591 reaction equation
C(=O)([O-])[O-].[K+].[K+].CO.[CH3:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:29])[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:27][CH3:28])[CH:21]=2)[CH2:12][CH2:11]1.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CC(CC(C)C)=O>[CH3:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([NH:16][C:17](=[O:29])[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:22]([O:27][CH3:28])[CH:21]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178490515HCID 178490515, compound

Product 1

HCID 178472972HCID 178472972, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

20.7 g of potassium carbonate and 5 ml of methanol were added to a solution of 28.9 g of N-(trans-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (Example 131) in 600 ml of methylisobutylketone. The solution was reacted for 30 minutes, while it was refluxed. Next, 27.7 ml of ethyl bromoacetate was added dropwise into the solution over about 20 minutes by means of a dropping funnel. Thereafter, the solution was stirred for 4 hours. After reaction, the solution was allowed to cool to room temperature. After the potassium carbonate has been filtered out from the filtrate, the solvent was removed in vacuo from the filtrate. The product obtained was recrystallized from methylene chloride/ether, yielding 35.2 g of N-(trans-4-methylcyclohexyl)-4-(ethoxycarbonylmethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 30 minutes, while it
  2. temperaturewas refluxed
  3. customAfter reaction
  4. filtrationAfter the potassium carbonate has been filtered out from the filtrate
  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-79aec66bc9424caaa44825dbd38fa071
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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