Reaction #11672

Reaction equation

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

methyl bromoacetate

ethyl acetate

sodium methoxide

→

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

Yield 72.4%

Solvents

water

tetrahydrofuran

Conditions

Workup

1. 1
   OtherThe organic phase was separated
2. 2
   Washwashed with water (25 mL)
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherAfter solvent evaporation under vacuum
5. 5
   Otherthe crude product was purified by reverse phase preparative HPLC

Procedure

(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