Reaktion #11672

Reaktionsgleichung

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

methyl bromoacetate

ethyl acetate

sodium methoxide

→

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

Ausbeute 72.4%

Lösungsmittel

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase was separated
2. 2
   Waschenwashed with water (25 mL)
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeAfter solvent evaporation under vacuum
5. 5
   Sonstigethe crude product was purified by reverse phase preparative HPLC

Vorschrift

(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).

Quelle