Hydrochloric Acid → HCID 58495458, compound

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Reaction Steps

Add 4M hydrogen chloride in dioxane (6.1 mL) to a solution of N-(tert-butoxycarbonyl)-4-[(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-amino]-benzylamine (0.678 g, 1.958 mmol) in anhydrous 1,4-dioxane (12.2 mL) at room temperature. After stirring at room temperature for 3 h, the reaction is a solid mass. Add more 1,4-dioxane (12.2 mL), DCM (24.4 mL) and more 4M hydrogen chloride in dioxane (6.1 mL), and stir overnight. Concentrate in vacuo and partition the residue between saturated aqueous NaHCO3 (200 mL) and DCM (500 mL). Dry the organic phase over Na2SO4, filter and concentrate in vacuo. The aqueous phase was extracted with DCM/iso-propanol (3:1, 4×200 mL). Dry the combined organic extracts over Na2SO4, filter, combine with the organic fraction isolated above and concentrate in vacuo. Purify by SCX chromatography eluting with DCM and DCM/2M ammonia in methanol (1:1) to obtain the title compound (0.519 g, 100%). MS (ES+) m/z: 247.2 (M+H)+.

Provenance & Evidence