Benzyl Alcohol → HCID 10379102, compound

Participants

Reaction Steps

A solution of Example 22B (0.11 g, 0.33 mmol), benzyl alcohol (0.07 mL, 0.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.080 g, 0.41 mmol), HOAT (0.045 g, 0.33 mmol), and N-methylmorpholine (0.055 mL, 0.50 mmol) in 3:1 dichloromethane/DMF (4 mL) at room temperature was stirred for 16 hours, diluted with dichloromethane, washed sequentially with aqueous NaHCO3, brine, 0.5M citric acid, and brine, dried (MgSO4), filtered, and concentrated. The residue was dissolved in 4M HCl in dioxane (2 mL), stirred for 1 hour, treated with water (1 mL), stirred for 1 hour, concentrated, and purified by reverse phase HPLC with acetonitrile/water to provide the desired product. MS (ESI) m/e 284 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.43–7.37 (m, 5H), 5.20 (s, 1.4H), 5.19 (m, 0.6H), 4.44 (m, 0.3H), 4.32 (m, 0.7H), 3.53 (m, 1H), 2.63 (m, 2H), 2.43 (m, 2H), 1.90–1.75 (m, 2H), 1.20–1.12 (m, 3H).

Provenance & Evidence