反応 #1478590

反応方程式

2-aminoacetophenone

D-biotin

N-methylmorpholine

isobutyl chloroformate

→

crude product 1c

収率 72.0%

Biotin ortho-acetophenone

収率 72.0%

溶媒

DMF

ether

反応条件

後処理

1. 1
   温度The solution is maintained
2. 2
   workup.STIRRINGstirred at room temperature for 3 h 30 min
3. 3
   その他evaporated to dryness
4. 4
   その他The precipitate obtained
5. 5
   ろ過is filtered
6. 6
   洗浄washed with water
7. 7
   その他The precipitate obtained
8. 8
   ろ過is filtered
9. 9
   洗浄washed with water
10. 10
    その他Recrystallization
11. 11
    workup.DISSOLUTIONby dissolving the product in MeOH in the hot state
12. 12
    その他reprecipitating by addition of water
13. 13
    ろ過The precipitate is filtered
14. 14
    洗浄washed with water

実験手順

The D-biotin (1 g, 4.1 mmol) is solubilized in 45 ml of anhydrous DMF in the hot state. The mixture is cooled to 0° C. under argon, and then N-methylmorpholine (590 μl, 5.33 mmol) and isobutyl chloroformate (840 μl, 6.60 mmol) are successively added. The mixture is kept stirred for 30 min, and then 2-aminoacetophenone (824 mg, 6.10 mmol) is added. The solution is maintained stirred at room temperature for 3 h 30 min, and then evaporated to dryness. The residue is taken up in 50 ml of water. The precipitate obtained is filtered, washed with water and then with 50 ml of MeOH in the hot state. The precipitate obtained is filtered and washed with water. Recrystallization is carried out by dissolving the product in MeOH in the hot state and reprecipitating by addition of water. The precipitate is filtered, washed with water, and then with ether to give 1.1 g (2.95 mmol, 72%) of crude product 1c.

出典