1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58504202, compound

Participants

Reaction Steps

The compound prepared in Example 230 (0.090 g) and lithium hydroxide hydrate (0.011 g) were combined in methanol (1 mL), tetrahydrofuran (1 mL) and water (0.1 mL) and allowed to stir for 48 hours. The reaction was concentrated, pumped to dryness and used without further purification. The crude acid was combined with the compound prepared in Example 9 (0.11 g, 0.31 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (0.069 g, 0.36 mmol), diisopropylethylamine (0.16 g, 1.2 mmol) and 1-hydroxybenzotriazole hydrate (0.049 g, 0.36 mmol) in dichloromethane (2.5 mL). The reaction was sonicated briefly to aid dissolution and then stirred for 24 hours. The crude reaction was concentrated and then dissolved in methanol and treated with 2N hydrochloric acid. After stirring for 15 minutes, this solution was concentrated and then partitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution. The organic phase was dried over magnesium sulfate, filtered, concentrated and purified by column chromatography using an eluant of 4% methanol/dichloromethane to provide the title compound (0.023 g) with the following physical data.

Provenance & Evidence