反応 #593948

反応方程式

Fmoc-Gly-OH

CH3ONHCH3

HOBt

WSCI.HCl

DIEA

→

Fmoc-Gly-N(CH3)OCH3

溶媒

DMF

反応条件

後処理

1. 1
   濃縮After the reaction solution was concentrated
2. 2
   workup.ADDITION10% aqueous citric acid solution was added
3. 3
   抽出the precipitated solid was extracted with AcOEt
4. 4
   洗浄The organic layer was washed with 10% aqueous citric acid solution, 5% NaHCO3 aqueous solution
5. 5
   乾燥sodium chloride aqueous solution, and dried over anhydrous Na2SO4

実験手順

Fmoc-Gly-OH, 1 g (3.36 mmol), 361.0 mg (3.70 mmol) of CH3ONHCH3 and 447.3 mg (3.53 mmol) of HOBt were dissolved in DMF. Under ice cooling, 677 mg (3.53 mmol) of WSCI.HCl and 1.94 mL (11.1 mmol) of DIEA were added to the solution, followed by stirring overnight. After the reaction solution was concentrated, 10% aqueous citric acid solution was added and the precipitated solid was extracted with AcOEt. The organic layer was washed with 10% aqueous citric acid solution, 5% NaHCO3 aqueous solution and satd. sodium chloride aqueous solution, and dried over anhydrous Na2SO4. The oily Fmoc-Gly-N(CH3)OCH3 product obtained by concentrating the solvent was dissolved in THF. Under ice cooling, 332 mg (0.726 mmol) of LiAlH4 was added by small portions to the solution over 15 minutes. After stirring at 0° C. for 30 minutes, 150 mL of diethyl ether and 150 mL of 20% citric acid aqueous solution were sequentially added to the reaction solution, which was then vigorously stirred for an hour. The organic layers were collected and the aqueous layer was again extracted with 150 mL of diethyl ether. The pooled organic layer was washed sequentially with 5% NaHCO3 aqueous solution, water, 10% citric acid aqueous solution, water and then satd. sodium chloride aqueous solution, and dried over anhydrous Na2SO4. The organic layer obtained was concentrated to give Fmoc-Gly-al as an oily substance.

出典