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With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; at 10 - 20℃; for 5h;Inert atmosphere;
Example 2 Boc-L-Lys(Boc)-OMe A 1 L three-neck flask equipped with addition funnel, nitrogen inlet, thermometer and mechanical stirrer was charged with a solution of Boc-L-Lys(Boc)-OH (59.37 g, 161 mmol, 94 wt % in EtOAc) in N,N-dimethylformamide (anhydrous) (300 mL). Whilst stirring, potassium carbonate (24.5 g, 177 mmol) was added, and the resulting suspension was cooled on an ice bath to an internal temperature of +10 C. Iodomethane (34.3 g, 242 mmol, 15.04 mL) was added dropwise over 30 min via the addition funnel, while keeping the internal temperature <20 C. The ice bath was removed and the reaction mixture was allowed to reach room temperature. TLC indicated complete consumption of the starting material after 4.5 h of stirring at room temperature. All volatiles were removed in vacuo, the resulting white slurry solidified on standing, and it was stored at -20 C. overnight. The resultant material was taken up in water (1 L) and sat'd. NaHCO3 (0.5 L), and then extracted with EtOAc (3*500 mL). The combined organic phases were washed with dilute brine (2*200 mL), brine (2*100 mL), then dried over Na2SO4 and concentrated. After stripping with heptane (2*200 mL), the title compound was isolated as a white solid (57.08 g, 97% yield). 1H-NMR (CDCl3): In agreement with structure. LCMS (NQAD detection): Purity >99%, mass in agreement with molecular formula (pos. m/z=361 [M+1]+, 383 [M+Na]+). Specific rotation: [α]D22=6.38 (c=1.72, CHCl3).
3 g
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;
Potassium carbonate (1.8 g, 13.0 mmol) and methyl iodide (0.65 mL, 10.4 mmol) were added to a solution of compound la (3.0 g, 8.7 mmol) in DMF (25 mL) and stirred at room temperature for 2 h. The completeness of the reaction was confirmed by TLC analysis. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with water, brine, dried over Na2SC>4 and evaporated under reduced pressure to yield 3.0 g of compound lb. LCMS: 361.1 (M+H)+.
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