Water → HCID 23729497, compound

Participants

Reaction Steps

To the 2-{5-[[2-(bis-cyclopropylmethyl-amino)-8-methyl-quinoline-3-ylmethyl]-(3,5-bistrifluoromethyl-benzyl)-amino]-tetrazol-2-yl}-ethanol (0.08 g, 0.126 mmol), (example 93), was added NaOH (0.010 g, 0.25 mmol) and water (1 mL). The reaction was stirred at room temperature for 15 min and then DCM (1 mL) was added followed by the addition of DMS (0.019 g, 0.15 mmol) and TBAB (0.002 g, 0.006 mmol). The reaction was continued for overnight. The solvent was evaporated and the aqueous layer was back extracted with DCM (2×10 mL). The combined organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated on rotavapor. The residue obtained was purified by preparative thin layer chromatography and eluted with 15% ethyl acetate and petroleum ether to get the desired product (0.30 g, 56%).

Provenance & Evidence