反应 #5822

反应方程式

N-tert-butoxycarbonyltyrosine methyl ester

sodium hydride

dimethylformamide

→

title compound

N-Tert-Butoxycarbonyl-O-(2-Methoxyethoxymethyl)Tyrosine Methyl Ester

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   其他After removing from the ice bath
2. 2
   workup.STIRRINGthe mixture was stirred at a room temperature for 30 minutes
3. 3
   workup.ADDITIONafter addition of 5.4 g of methoxyethoxymethyl chloride with ice cooling
4. 4
   workup.STIRRINGstirred for 15 hours
5. 5
   workup.ADDITIONThe reaction mixture was poured on ice, saturated with sodium chloride
6. 6
   萃取extracted twice with 800 ml of chloroform
7. 7
   干燥The extract was dried over magnesium sulfate
8. 8
   其他the solvent was evaporated under a reduced pressure
9. 9
   其他resulting residue
10. 10
    洗涤eluted with hexane/ethyl acetate (4:1)

实验过程

13.39 g of N-tert-butoxycarbonyltyrosine methyl ester was dissolved in 65 ml of tetrahydrofuran and 65 ml of dimethylformamide, and to the solution was added 1.9 g of 60% sodium hydride with stirring in an ice bath. After removing from the ice bath, the mixture was stirred at a room temperature for 30 minutes, and after addition of 5.4 g of methoxyethoxymethyl chloride with ice cooling, stirred for 15 hours allowing to warm to a room temperature. The reaction mixture was poured on ice, saturated with sodium chloride and extracted twice with 800 ml of chloroform. The extract was dried over magnesium sulfate and the solvent was evaporated under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (4:1) to obtain 13.85 g of the title compound in a colorless amorphous form.

来源