1-Hydroxy-2-naphthoic acid → HCID 58865420, compound

Participants

Reaction Steps

1-Hydroxy-naphthalene-2-carboxylic acid (142) (0.028 g, 0.148 mmol) was dissolved in DMF (1 mL), iPr2EtN (0.222 mmol) was added followed by 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate (HBTU) (0.062 g, 0.163 mmol) and the mixture was shaken in an 8 mL Teflon septum capped vial at room temperature for 20 minutes. N-(2,6-bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-pyridin-4-yl)-benzene-1,4-diamine (141) (0.08 g, 0.0986 mmol) was added and the mixture was shaken at room temperature for 16 h. LC-MS indicated complete coupling at this point. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), NaHCO3 (aqueous sat., 15 mL) and brine (15 mL) via extraction, dried over MgSO4 and concentrated to give an orange/green oil. Purification by flash chromatography using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes) gave the desired product (143) as a greenish-white powder upon concentration (0.063 g, 0.064 mmol, 65% yield). LC-MS (ESI): (exact mass: 981.53) m/e=982.6 [M+1]+ (100%).

Provenance & Evidence