Hydrochloric Acid → HCID 67111698, compound

Participants

Reaction Steps

Triethylamine (0.0716 mL, 0.515 mmol) was added to a slurry of 2-amino-3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)propanoic acid hydrochloride (0.110 g, 0.234 mmol) in THF (5.00 mL) and water (5.00 mL). The reaction mixture was cooled in ice bath and a solution of Boc2O (0.0868 g, 0.398 mmol) in THF (1 mL) was addded dropwise then the solution was stirred at ambient temperature for 18 h. The reaction mixture was diluted with water and EtOAc, pH was adjusterd to 5 with 1 N HCl, and the aq. layer was extracted with EtOAc; the combined organics were dried over MgSO4, filtered, and concentrated in vacuo. The material was purified by chiral SFC (Column: Chiralpak AD-H (21×250 mm, 5 micron); A: Liquid CO2; B: Isopropanol (0.2% DEA); Isocratic: 75:25 (A:B); Flow Rate: 70 mL/min; Outlet Pressure: 100 bar) to give (R)-2-(tert-butoxycarbonylamino)-3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)propanoic acid and (S)-2-(tert-butoxycarbonylamino)-3-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)propanoic acid. MS (ESI) m/z: calculated: 533.2; Observed: 534.1 (M++1).

Provenance & Evidence