methyl 2-amino-3-(3-hydroxyphenyl)propanoate synthesis

Yield:162536-44-9 4.97 g

Reaction Conditions:

with thionyl chloride at 20;Cooling with ice;

Steps:

1.A Methyl 2-amino-3-(3-hydroxyphenyl)propanoate (Intermediate 1A-a)

Methyl 2-amino-3-(3-hydroxyphenyl)propanoate (5.56 g, 30.76 mmol) was suspended in methanol (120 mL) and the mixture was cooled in an ice bath. Thionyl chloride (11.2 mL, 154 mmol) was added dropwise. The mixture was allowed to warm to RT and then stirred overnight. The solvent was evaporated and the residue dissolved in water (50 mL). After basifying the mixture using saturated aqueous sodium hydrogen carbonate, the product wasextracted into ethyl acetate (5 x 50 mL). The combined organic extracts were dried (Na2SO4) and evaporated to give the desired product as a white solid (4.97 g).LCMS (Method 4): Rt = 0.25 min mlz 196.1 [M+H]

References:

WO2019/121223,2019,A1 Location in patent:Page/Page column 31