Triethylamine → HCID 66654592, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of triphosgene (20 mg, 0.07 mmol, 0.33 eq.) in MeCN (0.3 mL) at −10° C. (acetone/ice bath), a solution of 2-(2-chlorophenyl)ethylamine (33 μL, 0.22 mmol, 1.10 eq.) and triethylamine (39 μL, 0.28 mmol, 1.30 eq.) in MeCN (2 mL) was added over a period of 15 min. The mixture was stirred for an additional 30 min at 0° C. and then a solution of (±)-[4-fluoro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl ester hydrochloride (73 mg, 0.20 mmol, 1.00 eq.) and triethylamine (78 μL, 0.56 mmol, 2.80 eq.) in MeCN (1 mL) was slowly added. The reaction mixture was slowly warmed to r.t. (ice bath during 30 min, then r.t.) and stirred at r.t. for 60 hours. The mixture was diluted with AcOEt, washed with water and sat. aq. NaCl soln., dried over MgSO4, filtered, and evaporated. To a solution of the crude product in DMF (0.9 mL), 1M aq. NaOH soln. (0.25 mL) was added. The solution was stirred at r.t. for 18 hours. The solution was acidified with 1M aq. HCl soln. (0.25 mL) then purified by prep. HPLC (column: Waters X-Bridge, 30×75 mm, 10 um, UV/MS, acidic conditions) to afford the title compound.

Provenance & Evidence