Reaction #87146

Reaction equation

water

potassium carbonate

4-methoxybenzoyl chloride

glycine methyl ester

→

methyl 2-(4-methoxybenzamido)acetate

Yield 86.6%

Solvents

THF

Conditions

Workup

1. 1
   ExtractionThe resulting mixture was extracted with EtOAc (200 ml×2)
2. 2
   DryingThe combined extracts were dried over anhydrous sodium sulfate
3. 3
   Concentrationconcentrated

Procedure

Saturated aqueous potassium carbonate (190 mL) and 4-methoxybenzoyl chloride (60.8 g, 358 mmol) were added to a solution of glycine methyl ester (30.0 g, 239 mmol) in THF (100 mL) at 0° C. The reaction mixture was stirred for 3 h at 0° C. and then poured into water (100 mL). The resulting mixture was extracted with EtOAc (200 ml×2). The combined extracts were dried over anhydrous sodium sulfate and concentrated to afford methyl 2-(4-methoxybenzamido)acetate (46.2 g, 86% yield) as a colorless solid, which was used directly without further purification.

Source