反応 #2286395

反応方程式

di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate

trifluoroacetic acid

→

product

収率 68.8%

[4-fluoro-2-(5-fluoro-pyridin-3-yl)-thiazol-5-yl]-carbamic acid tert-butyl ester

収率 68.8%

溶媒

DCM

反応条件

後処理

1. 1
   その他before quenched slowly with saturated NaHCO3 solution
2. 2
   その他The organic layer was separated
3. 3
   抽出the aqueous layer was extracted with dichloromethane (DCM)
4. 4
   乾燥The combined organic layer was dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   その他purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

実験手順

To a solution of di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate (320 mg, 0.77 mmol) in DCM (7 mL) was added trifluoroacetic acid (TFA) (0.7 mL). The solution was stirred at room temperature for 10 minutes, before quenched slowly with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane (DCM). The combined organic layer was dried over Na2SO4, filtered and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give product as a pale yellow solid (166 mg, 68%): mp 188-191° C.; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 1H), 8.46 (d, J=2.7 Hz, 1H), 7.85 (ddd, J=9.1, 2.6, 1.7 Hz, 1H), 6.92 (br s, 1H), 1.55 (s, 9H); ESIMS m/z 312 (M−1).

出典