1-Hydroxy-2-naphthoic acid → HCID 58865089, compound

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Reaction Steps

1-Hydroxy-naphthalene-2-carboxylic acid (142) (0.018 g, 0.096 mmol) was dissolved in DMA (2 mL), iPr2EtN (0.096 mmol) was added followed by HBTU (0.036 g, 0.096 mmol) and the mixture was shaken in an 8 mL Teflon septum capped vial at room temperature for 20 minutes. 4,6-bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-2-(4-aminophenyl-amino)-pyridine (168) (0.055 g, 0.0677 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) and the organic layer washed with water (15 mL), NaHCO3 (aqueous sat., 15 mL) and brine (15 mL) via extraction, dried over MgSO4 and concentrated to give a brown oil. Purification by flash chromatography on silica gel using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane for 30 min) gave the desired product (170) as an off-white powder upon concentration (0.042 g, 0.043 mmol, 64% yield). LC-MS (ESI): (exact mass: 981.53) m/e=982.6 [M+H+].

Provenance & Evidence