反応 #1478588

反応方程式

D-biotin

3-aminoacetophenone

N-methylmorpholine

N-methylmorpholine

isobutyl chloroformate

→

1a

収率 70.0%

Biotin meta-acetophenone

収率 70.0%

溶媒

DMF

DMF

反応条件

後処理

1. 1
   温度The solution is maintained
2. 2
   workup.STIRRINGstirred at 0° C. for 2 hours (h)
3. 3
   その他evaporated to dryness
4. 4
   workup.ADDITION50 ml of water are added
5. 5
   その他The precipitate obtained
6. 6
   ろ過is filtered
7. 7
   洗浄washed with water, CH2Cl2 and ether
8. 8
   その他to give 1.2 g (80%) of crude product 1a
9. 9
   その他Recrystallization from the MeOH—H2O pair

実験手順

The D-biotin (1.0 gram (g), 4.1 millimoles (mmol) is solubilized in 45 milliliters (ml) of anhydrous DMF in the hot state. The mixture is cooled to 0° C. under argon, and then N-methylmorpholine (590 microliters (μl), 5.33 mmol) and isobutyl chloroformate (840 μl, 6.60 mmol) are successively added. The mixture is kept stirred for 30 minutes (min), and then 3-aminoacetophenone (824 mg, 6.10 mmol) and N-methylmorpholine (480 μl, 4.35 mmol) in 10 ml of DMF are added. The solution is maintained stirred at 0° C. for 2 hours (h), and then evaporated to dryness. The residue is taken up in 3 ml of MeOH, and then 50 ml of water are added. The precipitate obtained is filtered, washed with water, CH2Cl2 and ether to give 1.2 g (80%) of crude product 1a. Recrystallization from the MeOH—H2O pair gives 1a (1.01 g, 70%) in the form of a white powder.

出典