反应详情

A solution of 2-(4-benzyloxy-3-methoxyphenyl)propionic acid (5.0 g, 17.5 mmoles) and 4-methylmorpholine (2.0 mL, 17.5 mmoles) in ethyl acetate (170 mL) at 0° C. was treated with isobutyl chloroformate (2.26 mL, 17.5 mmoles). The resulting white slurry was stirred for 20 minutes. A solution of racemic 2-octylamine (2.7 g, 21 mmoles) in ethyl acetate (10 mL total solution) was added to the suspension which was then stirred for 3 hours. The mixture was extracted with 1M hydrochloric acid (3×50 mL), with a saturated sodium bicarbonate solution (3×50 mL), with brine (1×50 mL) and dried over magnesium sulfate. The ethyl acetate was rotary evaporated affording N-2-octyl-2-(4-benzyloxy-3-methoxyphenyl)proprionamide as a white solid which was crystallized from ether/methylene chloride to give 4.55 g. This racemic mixture of diastereomers was separated by silica gel chromatography.

1. stirringwas then stirred for 3 hours
2. extractionThe mixture was extracted with 1M hydrochloric acid (3×50 mL), with a saturated sodium bicarbonate solution (3×50 mL), with brine (1×50 mL)
3. dry with materialdried over magnesium sulfate
4. customThe ethyl acetate was rotary evaporated