反応 #314407

反応方程式

BOC-hydroxyproline

N,N-diisopropylethylamine

dimethylamine hydrochloride

→

L-trans-4-Hydroxyproline N,N-dimethylamide hydrochloride

溶媒

dichloromethane

dichloromethane

HCl dioxan

反応条件

後処理

1. 1
   洗浄washed with 0.3M KHSO4, saturated sodium bicarbonate solution and brine
2. 2
   乾燥dried over MgSO4
3. 3
   濃縮concentrated in vacuo
4. 4
   その他to give a colourless gum
5. 5
   workup.STIRRINGstirred at room temperature for 1 hr
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was azeotroped with toluene and diethyl ether
8. 8
   その他to give a white solid

実験手順

To a solution of BOC-hydroxyproline (2.99 g, 13.89 mmol) in dichloromethane (100 ml) were added N,N-diisopropylethylamine (3.7 ml, 21.24 mmol), 4-(dimethylamino)pyridine (1.74 g, 14.24 mmol), dimethylamine hydrochloride (1.72 g, 21.09 mmol) and WSCDI (3.17 g, 16.68 mmol). The mixture was stirred at room temperature for 30 hr. The mixture was diluted with dichloromethane (100 ml) and washed with 0.3M KHSO4, saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated in vacuo to give a colourless gum. This crude material was taken up in 4N HCl/dioxan (50 ml) and stirred at room temperature for 1 hr and then concentrated in vacuo. The residue was azeotroped with toluene and diethyl ether to give a white solid; yield 0.45 g (17%).

出典