反应详情

温度

0 °C

A mixture of 10.0 g (41 mmoles) biotin (1) and 800 ml N,N-dimethylformamide was stirred until all of the biotin had dissolved. Then 12.8 ml (53.8 mmoles) of tributylamine was added and the solution stirred for 10 minutes. To this solution was added 6.4 ml (49.4 mmoles) of isobutyl chloroformate followed by stirring for 30 minutes. This solution was then slowly added to a cold (-5° C.) solution of 5.80 g (49.4 mmoles) 6-amino-1-hexanol in 800 ml N,N-dimethylformamide. Addition took place over a 30-minute period, and the temperature of the reaction mixture was maintained at 0° C. during the addition. After addition was complete, the reaction mixture was stirred at 0° C. for 3 hours, then allowed to warm to 20° C. The solution was evaporated under high vacuum (2 Torr) and the residue was dissolved in 400 ml of anhydrous ethanol with heating. The solution was stored at -20° C. overnight, filtered, and the white crystalline precipitate washed with anhydrous ethanol. The washed precipitate was allowed to air dry to yield 13.4 g of white crystals, with an Mp of 170°-176° C. Recrystallization from anhydrous ethanol yielded material of MP 179°-181° C.

1. dissolutionhad dissolved
2. stirringby stirring for 30 minutes
3. additionAddition
4. customover a 30-minute
5. additionAfter addition
6. stirringthe reaction mixture was stirred at 0° C. for 3 hours
7. temperatureto warm to 20° C
8. customThe solution was evaporated under high vacuum (2 Torr)
9. dissolutionthe residue was dissolved in 400 ml of anhydrous ethanol
10. temperaturewith heating
11. waitThe solution was stored at -20° C. overnight
12. filtrationfiltered
13. washthe white crystalline precipitate washed with anhydrous ethanol
14. customto air dry