反応 #5999

反応方程式

benzyloxycarbonyl chloride

hydrochloric acid

sodium borate

dopamine hydrochloride

sodium hydroxide

sodium hydroxide

→

desired compound

収率 96.5%

N-carbobenzoxydopamine

収率 96.5%

溶媒

water

反応条件

後処理

1. 1
   その他To the solution thus obtained
2. 2
   温度to maintain the pH value of the reaction mixture to 9
3. 3
   その他stirring for 2 hours
4. 4
   抽出extracted with diethyl ether
5. 5
   乾燥Next, it was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   洗浄After washing the residue with petroleum ether
8. 8
   その他the crude crystals thus obtained
9. 9
   その他were recrystallized from ethanol/n-hexane (1 : 1 by volume)

実験手順

38.2 g (100 mmol) of sodium borate and 18.9 g (100 mmol) of dopamine hydrochloride were dissolved in 250 ml of water. To the solution thus obtained, was added a 2 N sodium hydroxide solution under a nitrogen gas stream to adjust the pH value to 9. Then 17.1 g (100 mmol) of benzyloxycarbonyl chloride was added dropwise thereto while stirring at 15° C. for 4 hours. Simultaneously, a 2 N sodium hydroxide solution was added to maintain the pH value of the reaction mixture to 9. After continuing the stirring for 2 hours, the mixture was adjusted to pH 1 to 2 with hydrochloric acid and then extracted with diethyl ether. Next, it was dried over anhydrous magnesium sulfate and the solvent was distilled off. After washing the residue with petroleum ether, the crude crystals thus obtained were recrystallized from ethanol/n-hexane (1 : 1 by volume). Thus 27.6 g (yield: 96.5% of the desired compound (m.p.: 134°- 135 ° C.) was obtained in the form of white crystals.

出典