Triethylamine → 3-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-Boc-diaminobutyric acid (25 g, 115 mmol), triethylamine (35 g, 344 mmol), and hydroxybenzotriazole (19.3 g, 143 mmol) in 0.5 L of THF is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 g, 143 mmol). The solution is heated to 60° C. over 15 minutes. A white precipitate forms and the solution is kept at 60° C. for 4 hours. After this time, the solution is filtered and the collected liquid is concentrated. The crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (19.6 g, 98 mmol) as a white solid.

Provenance & Evidence