反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
3.0 g (7.1 mmol) of (S)-N-(α-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide (compound of Description 4) were dissolved, under nitrogen atmosphere, in 60 ml of CH2Cl2 and 1.2 ml (8.5 mmol) of TEA were added; the solution was cooled to 0° C. and 2.7 g (8.5 mmol) of (9-fluorenylmethoxy carbonyl)glycinyl chloride (FMOC-glycinyl chloride), dissolved in 60 ml of CH2Cl2, were added dropwise. The reaction mixture was stirred at room temperature for 3 hours and then washed with sat. sol. NaCl, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl, dried over Na2SO4 and evaporated in vacuo to dryness. The crude product was purified by gradient flash column chromatography on 230-400 mesh silica gel, utilising a mixture of hexane/EtOAc 1:1 as starting eluent and a mixture of EtOAc/MeOH 9:1 as final eluent. The product (5.0 g) was dissolved in 100 ml of a 10% solution of diethylamine in DMF and stirred at room temperature for 30 minutes. The reaction mixture was then evaporated in vacuo and purified by gradient flash column chromatography on 230-400 mesh silica gel, utilising a mixture of EtOAc/MeOH 9:1 as starting eluent and a mixture of EtOAc/MeOH 7:3 as final eluent, to yield 0.6 g of the title compound.
WORKUP
后处理
- additionwere added dropwise
- washwashed with sat. sol. NaCl, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl
- dry with materialdried over Na2SO4
- customevaporated in vacuo to dryness
- customThe crude product was purified by gradient flash column chromatography on 230-400 mesh silica gel, utilising
- additiona mixture of hexane/EtOAc 1:1
- additiona mixture of EtOAc/MeOH 9:1 as final eluent
- dissolutionThe product (5.0 g) was dissolved in 100 ml of a 10% solution of diethylamine in DMF
- stirringstirred at room temperature for 30 minutes
- customThe reaction mixture was then evaporated in vacuo
- custompurified by gradient flash column chromatography on 230-400 mesh silica gel, utilising
- additiona mixture of EtOAc/MeOH 9:1
- additiona mixture of EtOAc/MeOH 7:3 as final eluent