Reacción #59397

Ecuación de reacción

(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril

methyl bromoacetate

ethyl acetate

sodium methoxide

→

(R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril

Rendimiento 72.4%

Disolventes

water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic phase was separated
2. 2
   Lavadowashed with water (25 mL)
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   OtroAfter solvent evaporation under vacuum
5. 5
   Otrothe crude product was purified by reverse phase preparative HPLC

Procedimiento

(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (26 mg), as prepared in Example 5, was dissolved in tetrahydrofuran (5 mL) at room temperature under argon. To the stirring solution was added methyl bromoacetate (31 mg), followed by sodium methoxide (26 mg). The resulting suspension was stirred for 30 min before dilution with ethyl acetate (25 mL) and water (25 mL). The organic phase was separated, washed with water (25 mL), and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide (R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril (24 mg).

Fuente