Hydrochloric Acid → HCID 131435015, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Ethyl 4-[(tert-butylsulfinyl)amino]-2,2-dimethyl-4-phenylbutanoate from Step B (0.19 g, 0.55 mmol) in MeOH (10 mL) was added anhydrous HCl (gas, bubbled in for about 1 minute). After 20 minutes, nitrogen was bubbled though the reaction mixture for about 20 minutes. The initial solvent was removed in vacuo, and then more MeOH was added and removed in vacuo. The residue was then dissolved in MeOH (20 mL) and treated with triethylamine (0.22 g, 2.2 mmol). The solvent was once again removed in vacuo. This residue was then treated with toluene (10 mL) and triethylamine (0.22 g, 2.2 mmol) before being heated to 100° C. for 15 hours. After cooling to ambient temperature the solvent was removed in vacuo and the residue was partitioned between diethyl ether (50 mL) and 1 M HCl (50 mL). The organics were then successively washed with another volume of 1 M HCl, water and lastly saturated brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound which was used without further purification. MS: m/z=190 (M+1).

Provenance & Evidence