[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[C@@H:10]([CH3:12])[OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:16](Cl)[CH:17]=[CH:18][CH3:19].C([O-])(O)=[O:22].[Na+].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:16]([O:11][C@H:10]([CH3:12])[C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])[C:13]([OH:15])=[O:14])(=[O:22])/[CH:17]=[CH:18]/[CH3:19]
To a solution of Boc-L-Threonine (0.44 g 2.0 mmol) in 10.0 ml of DCM was added crotyl chloride (0.32 g, 3.0 mmol) at RT followed by the addition of catalytic amount of DMAP and TEA (1.0 ml, 6 mmol). The reaction mixture was stirred for 10 h at RT. Aqueous NaHCO3 solution (10 mL) was added to quench the reaction. After 2 hours, 1N HCl aqueous solution was added slowly to PH˜3. The DCM layer was collected and the aqueous was extracted by DCM (2×10 mL). The organic layer was dried over Na2SO4, filterd and the solvent was removed to provide the crude product.
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