Ethanol → ethyl 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionate
Reaction equation
S(Cl)(Cl)=O.[CH2:5]([NH:12][CH:13]1[CH2:19][C:18]2[CH:20]=[C:21]([O:24][C:25]([CH3:30])([CH3:29])[C:26]([OH:28])=[O:27])[CH:22]=[CH:23][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+].[CH2:36](O)[CH3:37]>>[CH2:5]([NH:12][CH:13]1[CH2:19][C:18]2[CH:20]=[C:21]([O:24][C:25]([CH3:30])([CH3:29])[C:26]([O:28][CH2:36][CH3:37])=[O:27])[CH:22]=[CH:23][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1Participants
Conditions
- Temperature
- -10 °C
Procedure
Thionyl chloride (0.2 ml) was added dropwise to ethanol (5 ml) with stirring at -10° C. After stirring for ten minutes, 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionic acid (0.49 g) was added portionwise to the mixture. The reaction mixture was stirred at ambient temperature for 1 hour and then refluxed for 3 hours. After cooling, the mixture was poured into an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with chloroform-methanol (100:1) to give ethyl 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionate (0.43 g).
Workup
- stirringAfter stirring for ten minutes
- stirringThe reaction mixture was stirred at ambient temperature for 1 hour
- temperaturerefluxed for 3 hours
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel with chloroform-methanol (100:1)
Sources & evidence
- ORD record
- ord-6ebccb6c61f34640b1a0fd1246edf423
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387710
Reaction notes
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