Veratric Acid → HCID 59773004, compound

Participants

Reaction Steps

3,4-Dimethoxy benzoic acid 1.04 g (5.72 mmol) was dissolved in 30 mL tetrahydrofuran, to this mixture was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 1.4 g (6.6 mmol), triethylamine 0.66 g (5.72 mmol), after 30 minutes 1-hydroxybenzotriazole 0.77 g (5.72 mmol) was added. The mixture was stirred one hour. To this mixture was added 2-{[naphthalen-2-ylmethyl]-amino]-methyl}-pyrrolidin-1-carboxylic acid tert-butyl ester 1.5 g (4.4 mmol). The mixture was stirred 1 night at room temperature. Added 50 mL of saturated sodium bicarbonate and extract with ethyl acetate 3 times 100 mL. The combined organic layer was dried over magnesium sulfate, filtered, and concentrated under vacuum. Purification over silica gel hexane: 1-dichloromethane: 1, lead to 1.1 g white powder. LC-MSD, m/z for: C30H36N2O5 [M+H]: 505.2. LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 7 minutes: 5.0 min.

Provenance & Evidence