反应详情

A 2-dram vial containing a small stirbar was charged with (R)-2-(tert-butoxycarbonylamino)-2-(1-methylcyclohexyl)acetic acid (10d) (11 mg, 0.04 mmol), CH2Cl2 (1 mL), 4-dimethylaminopyridine (2 mg, 0.02 mmol, 0.5 equiv), benzyl alcohol (20 μL, 0.2 mmol, 5 equiv), and EDC (20 mg, 0.1 mmol, 2.5 equiv). The solution was stirred at room temperature for 3 h, and then diluted with 10 mL Et2O. The mixture was washed with water (2×10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (7:1 hexanes/Et2O) and analyzed by chiral HPLC analysis: (AS-H, 1 mL/min, 2% IPA/hexanes, 210 nm): tR(minor)=6.84 min, tR(major)=8.13 min.

1. additionA 2-dram vial containing a small stirbar
2. washThe mixture was washed with water (2×10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
3. dry with materialThe organic layer was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel (7:1 hexanes/Et2O)
6. custom=6.84 min
7. customtR(major)=8.13 min.