Réaction #59397

Équation de réaction

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

methyl bromoacetate

ethyl acetate

sodium methoxide

→

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

Rendement 72.4%

Solvants

water

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreThe organic phase was separated
2. 2
   Lavagewashed with water (25 mL)
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   AutreAfter solvent evaporation under vacuum
5. 5
   Autrethe crude product was purified by reverse phase preparative HPLC

Mode opératoire

(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).

Source