[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5](CC=C)[C:6]([O:8]C(C)(C)C)=[O:7].N1[C:22]([CH3:23])=[CH:21]C=CC=1C.[Si:25](OS(C(F)(F)F)(=O)=O)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[Cl-].[NH4+]>C(Cl)Cl>[Si:25]([O:8][C:6]([NH:5][CH:4]([CH2:23][CH:22]=[CH2:21])[C:3]([O:2][CH3:1])=[O:16])=[O:7])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]
To a methylene chloride solution (1.5 ml) of N-(t-butoxycarbonyl)-allylglycine methyl ester (183 mg, 0.8 mmol) and 2,6-lutidine (0.186 ml, 1.6 mmol) was added t-butyldimethylsilyltrifluoromethane sulfonate (TBDMSOTf) (0.275 ml, 1.2 mmol) at room temperature in a nitrogen atmosphere. After the mixture was stirred for 15 minutes, a saturated aqueous solution of ammonium chloride (3 ml) was added to quench the reaction and extraction with ether was conducted. The organic layer was dried over anhydrous magnesium sulfate and filtered. By distilling off the solvent under vacuum, the titled compound was obtained in an amount of 260 mg.
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