反応 #5822

反応方程式

N-tert-butoxycarbonyltyrosine methyl ester

sodium hydride

dimethylformamide

→

title compound

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

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他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
   抽出extracted twice with 800 ml of chloroform
7. 7
   乾燥The extract was dried over magnesium sulfate
8. 8
   その他the solvent was evaporated under a reduced pressure
9. 9
   その他resulting residue
10. 10
    洗浄eluted with hexane/ethyl acetate (4:1)

実験手順

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.

出典