Reaction equation
C[Si](I)(C)C.[CH3:6][N:7]1[C:13](=[O:14])[CH:12]([NH:15]C(=O)OC)[CH2:11][C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]=2[CH2:8]1.C(OCC)(=O)C>ClCCl>[NH2:15][CH:12]1[CH2:11][C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]=2[CH2:8][N:7]([CH3:6])[C:13]1=[O:14]Participants
Procedure
0.6 ml of trimethylsilyl iodide is added to a solution of 203 mg (0.93 mmol) of product 2 in 10 ml of dichloromethane, and the mixture is then refluxed for 3 hours. After cooling to room temperature and adding 50 ml of ethyl acetate, the organic phase is extracted with 2×25 ml of 1N hydrochloric acid solution. The aqueous phases are combined, cooled and then basified by addition of 5N sodium hydroxide. The basic aqueous phases are then saturated with NaCl, and then extracted with 3×25 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulfate and evaporated under reduced pressure to give an oily residue. This residue is chromatographed on silica gel, eluting with a 90/10 dichloromethane/methanol mixture. 100 mg (57%) of the expected product 3 are obtained in the form of an oil.
Workup
- temperaturethe mixture is then refluxed for 3 hours
- extractionthe organic phase is extracted with 2×25 ml of 1N hydrochloric acid solution
- temperaturecooled
- additionbasified by addition of 5N sodium hydroxide
- extractionsaturated with NaCl, and then extracted with 3×25 ml of ethyl acetate
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- customto give an oily residue
- customThis residue is chromatographed on silica gel
- washeluting with a 90/10 dichloromethane/methanol mixture
Sources & evidence
- ORD record
- ord-36c906b80d454134ba87a400e65e03f4
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550453B2
Linked notes
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