反应详情

温度

0 °C

0.448 g of 60% NaH/oil (0.27 g, 11.1 mM of NaH) was added to 40 mL of dry THF and cooled to 0° C. 1.21 g (5.08 mM of CBZ-serine was added dropwise as a dry DMF solution (10 mL) over 5 minutes. The resulting mixture was stirred at 0° C. for 1 hr. 2.00 g (5.58 mmoles) of 3-[2-(2-phenyl-4-oxazolyl)ethoxy]benzyl bromide, prepared as described in Example 22, Part B, was also added dropwise as a dry DMF solution (10 mL) over 5 minutes. The final mixture was stirred for 5 h at 0° C. and was then allowed to warm to ambient over 12 h. The reaction was quenched with 20 mL of methanol and one equivalent of HCl. After concentrating to a small volume under reduced pressure, the mixture was diluted with 200 mL EtOAc, washed with 200 mL water (2×) and 200 mL brine. The organic phase was dried over MgSO4, filtered and concentrated to a yellow, opaque oil. The product was purified using silica column chromatography, (25:5:1 CHCl3:MeOH:NH4OH>>>3:4 MeOH:EtOAc), and recrystallized from Et2O. to provide 714 mg 49.6%) of product as a white, waxy solid.

1. temperatureto warm
2. waitto ambient over 12 h
3. concentrationAfter concentrating to a small volume under reduced pressure
4. additionthe mixture was diluted with 200 mL EtOAc
5. washwashed with 200 mL water (2×) and 200 mL brine
6. dry with materialThe organic phase was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated to a yellow, opaque oil
9. customThe product was purified
10. customrecrystallized from Et2O
11. customto provide 714 mg 49.6%) of product as a white, waxy solid