反応 #972788

反応方程式

glyceryl monooleate

Phosphorus oxychloride

2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid

→

3-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetoxy)-2-hydroxypropyl oleate

溶媒

pyridine

pyridine

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise over 5 mins
2. 2
   workup.STIRRINGThe mixture is stirred at 0° C. for a further 3 hours and 1 hour at 20° C.
3. 3
   その他quenched by addition of water (1 mL)
4. 4
   その他Volatile solvents are removed in vacuo and DCM (200 mL)
5. 5
   workup.ADDITIONadded
6. 6
   洗浄The organic phase is washed with water (1×50 mL), saturated sodium carbonate solution (1×50 mL) and brine (1×50 mL)
7. 7
   乾燥dried over Na2SO4
8. 8
   濃縮concentrated to dryness
9. 9
   その他purified by column chromatography (acetone/DCM eluent)

実験手順

Phosphorus oxychloride (2.4 mmol) is added dropwise over 5 mins to a solution of 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (810 mg, 2.0 mmol) in pyridine (20 mL) at 0° C. The mixture is stirred at 0° C. for a further 1 hour and then glyceryl monooleate (715 mg, 2.0 mmol) dissolved in pyridine (5 mL) is added dropwise over 5 mins. The mixture is stirred at 0° C. for a further 3 hours and 1 hour at 20° C. and then quenched by addition of water (1 mL). Volatile solvents are removed in vacuo and DCM (200 mL) added. The organic phase is washed with water (1×50 mL), saturated sodium carbonate solution (1×50 mL) and brine (1×50 mL), dried over Na2SO4, concentrated to dryness and purified by column chromatography (acetone/DCM eluent) to provide 3-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetoxy)-2-hydroxypropyl oleate.

出典