Ethyl bromoacetate → HCID 178472986, compound

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

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: