Ethyl 2-phenylacrylate → Ethyl 3-((3-ethoxy-3-oxopropyl)(methyl)amino)-2-phenylpropanoate
Reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[CH3:14][NH:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[CH2:21]([O:20][C:18]([CH2:17][CH2:16][N:15]([CH3:14])[CH2:3][CH:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:1]([O:11][CH2:12][CH3:13])=[O:10])=[O:19])[CH3:22]Participants
Procedure
184.47 g of ethyl atropate (of Example 1c) are added dropwise, over a 20 minute period, to 132.16 g of ethyl β-methylaminopropionate (of Example 1a). The mixture is stirred for 18 hours at room temperature under a nitrogen atmosphere. The mixture is combined with 1.8 l. of ether and then the resultant mixture is extracted with two 800 ml portions of 2 N hydrochloric acid. The acid solution is extracted with two 150 ml portions of ether. The aqueous extracts are basified with 50 weight percent aqueous NaOH solution and then extracted with three 900 ml portions of ether. The ether extracts are combined and dried for 18 hours over MgSO4. The combined ether portions are filtered and concentrated in vacuo to yield ethyl N-(2-ethoxycarbonylethyl)-3-methylamino-2-phenylpropionate.
Workup
- extractionof ether and then the resultant mixture is extracted with two 800 ml portions of 2 N hydrochloric acid
- extractionThe acid solution is extracted with two 150 ml portions of ether
- extractionextracted with three 900 ml portions of ether
- dry with materialdried for 18 hours over MgSO4
- filtrationThe combined ether portions are filtered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d31475373bff433d98b94ce9a65d34d6
- Source dataset
- uspto-grants-1981_11
- Patent number
- US04302590
Reaction notes
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