Hydrochloric Acid → HCID 66894003, compound

Participants

Reaction Steps

A solution of 2-(tert-butyoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (2.00 g, 7.21 mmol), N-hydroxyacetamidine (1.39 g, 18.8 mmol), [3-(dimethylamino)propyl]ethyl carbodiimide hydrochloride (3.04 g, 15.9 mmol), and 1-hydroxybenzotriazole (1.55 g, 1.01 mmol) was heated to 100° C. for 18 hours, then cooled to rt and concentrated in vacuo. The resultant residue was redissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, concentrated in vacuo, and subjected to silica gel chromatography from 0 to 20% ethyl actate in hexanes. To a solution of the resultant compound (0.600 g, 1.90 mmol) was added 4 N HCl in dioxane (1.42 mL, 4.26 mmol). After 2 hours, the reaction was concentrated in vacuo to provide the title compound as a beige solid that gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 216.2. This crude intermediate was used to prepare Example 21, by the procedure described for Example 1.

Provenance & Evidence