Dimethylformamide → HCID 90060119, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate (12 g, 40.63 mmol, 1 eq.) was dissolved in dehydrated DMF (30 mL), and potassium carbonate (6.177 g, 44.695 mmol, 1.1 eq.) and 1-iodobutane (5.55 mL, 48.756 mmol, 1.2 eq.) were added to the solution, which was stirred at 40° C. for a whole day and night and cooled to room temperature. The mixture was diluted with ethyl acetate, washed 3 times with water, and then with a saturated aqueous solution of ammonium chloride, and dried over anhydrous sodium sulfate. The organic layer was filtered and the solvent was distilled off. The residue was purified by aminosilica gel column chromatography (by elution with dichloromethane) to obtain the desired compound, (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-butoxyphenyl)propanoate as a white solid (11.842 g, 83% yield).

Provenance & Evidence