反应 #469658

反应方程式

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-1H-indol-5-yl]-1-methylethyl]-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]carbamate

sodium bicarbonate

2-ethylbutyryl chloride

2-ethylbutyric acid

oxalyl chloride

→

(R)-3-[5-[2-[N-(tert-butoxycarbonyl)-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-7-carbamoyl-1H-indol-1-yl]propyl 2-ethylbutyrate

收率 71.2%

溶剂

pyridine

反应条件

后处理

1. 1
   workup.ADDITIONwas added to the solution
2. 2
   萃取the mixture was extracted with ethyl acetate
3. 3
   洗涤The ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine subsequently
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   其他The solvent was removed in vacuo
6. 6
   其他the residue was purified by column chromatography on silica gel (eluent:hexane/ethyl acetate=2/1)

实验过程

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-1H-indol-5-yl]-1-methylethyl]-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]carbamate (2.00 g) was dissolved in dry pyridine (3 ml), and 2-ethylbutyryl chloride (0.54 g) prepared from 2-ethylbutyric acid and oxalyl chloride was added to the solution. After the mixture was stirred overnight at room temperature, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution and brine subsequently, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel (eluent:hexane/ethyl acetate=2/1) to give white amorphous (R)-3-[5-[2-[N-(tert-butoxycarbonyl)-N-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-7-carbamoyl-1H-indol-1-yl]propyl 2-ethylbutyrate (1.66 g).

来源