Dibutyltin oxide → HCID 178511774, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of {2-[4-(4-cyanobenzyl)-4-cyclohexylcarbamoyl-piperidin-1-yl]-2-oxo-1-thiophen-2-ylmethyl-ethyl}-carbamic acid tert-butyl ester (9.77 mmol; 5.85 g) (prepared as in Example 1, substituting 4-cyanobenzylbromide for 4-biphenylmethyl bromide and cyclohexylamine for cyclohexylmethylamine), in dimethoxyethane (3 mL) was added trimethylsilyl azide (0.67 mmol; 0.088 mL) and dibutyltin oxide (0.201 mmol; 53.15 mg). The resulting mixture was heated at 100° C. for 18 hours and then purified via reverse phase HPLC. The desired fractions were collected and lyophilized, and the residue was dissolved in THF (2 mL) and a 4N HCl solution in 1,4-dioxane (4 mL) was added. The resulting solution was stirred for 5 hours at room temperature and evaporated. The residue was triturated with diethyl ether and dried under vacuum to yield 1-(2-(S)-amino-3-thiophen-2-yl-propionyl)-4-[4-(1H-tetrazol-5-yl)-benzyl]-piperidine-4-carboxylic acid cyclohexylamide as a hydrochloride salt.

Provenance & Evidence