Reacción #5822

Ecuación de reacción

N-tert-butoxycarbonyltyrosine methyl ester

sodium hydride

dimethylformamide

→

title compound

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 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
   Extracciónextracted twice with 800 ml of chloroform
7. 7
   SecadoThe extract was dried over magnesium sulfate
8. 8
   Otrothe solvent was evaporated under a reduced pressure
9. 9
   Otroresulting residue
10. 10
    Lavadoeluted with hexane/ethyl acetate (4:1)

Procedimiento

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.

Fuente