반응 #155592
ord-c3b719c3ed9c4ec89331bebedfe9b317
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반응물
시약
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후처리
- 1기타partitioned between ethyl acetate (25 mL)
- 2기타The layers were separated
- 3추출the aqueous layer was extracted further with ethyl acetate (3×25 mL)
- 4세척The combined organics were then washed sequentially with water (100 mL) and with brine (100 mL)
- 5건조dried over sodium sulfate
- 6여과filtered
- 7농축The filtrate was concentrated under reduced pressure
- 8기타to yield a white solid
- 9세척the resulting solution was washed with 1 N sodium hydroxide (3×25 mL), water (100 mL), and brine (100 mL)
- 10건조The organic layer was dried over sodium sulfate
- 11여과filtered
- 12농축concentrated under reduced pressure
실험 절차
Lithium triethylborohydride (1.13 mL, 1.13 mmol) was added to a solution of N-[(4aR,6R,8aS)-8a-(2,4-difluoro-5-{[(2,2,2-trifluoroethyl)amino]methyl}phenyl)-6-(fluoromethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C27) (60 mg, 0.11 mmol) in tetrahydrofuran (4 mL). The reaction mixture was allowed to stir at room temperature for 16 hours and then partitioned between ethyl acetate (25 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL). The layers were separated and the aqueous layer was extracted further with ethyl acetate (3×25 mL). The combined organics were then washed sequentially with water (100 mL) and with brine (100 mL), dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a white solid. The organic crude was re-dissolved in dichloromethane (20 mL) and the resulting solution was washed with 1 N sodium hydroxide (3×25 mL), water (100 mL), and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the product as an orange solid (60 mg), which was taken directly to the following step. LCMS m/z 514 [M+H+].