Glycine, N-(cyclopropylcarbonyl)- (9CI) synthesis

Yield:64513-70-8 87.4%

Reaction Conditions:

with anhydrous sodium carbonate;sodium hydroxide in tetrahydrofuran;lithium hydroxide monohydrate at 0 - 20; for 4 h;

Steps:

74 Preparation of (cyclopropanecarbonyl)glycine:

To a solution of glycine (6 g, 79.9 mmol, 1 eq) in THF (100 mL) and water (100 mL) were added sodium hydroxide (3.84 g, 96 mmol, 1.20 eq) and sodium carbonate (10.20 g, 96.2 mmol, 1.20 eq) in one portion at 20 °C under a nitrogen atmosphere. Cyclopropanecarbonyl chloride (88.4 mmol, 8.03 mL, 1.11 eq) was added to the mixture at 0 °C, and the resulting reaction mixture was stirred at 20 °C for 4 hours. Completion of the reaction was confirmed using TLC analysis. The residue was poured into 1N HCl to adjust the pH of the mixture to 2. The aqueous phase was extracted with EA (100 mL x 3). The combined organic phase was washed with brine (100 mL x 3), dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The reaction was washed with EA (20 mL) and concentrated in vacuo to afford (cyclopropanecarbonyl)glycine (10 g, 69.9 mmol, 87.4% yield) as a white solid.

References:

WO2021/231474,2021,A1 Location in patent:Paragraph 0551