Methanol → HCID 59118190, compound

Participants

Reaction Steps

To a solution of 77.2 mg (0.11 mmol) methyl 4-[((2R)-2-{[(tert-butoxycarbonyl)((2R)-2-(3-pyridinyl)-2-{[(1,1,2,2-tetramethylpropyl)silyl]oxy}ethyl)amino]-methyl}-3,4-dihydro-2H-chromen-6-yl)methyl]benzoate (Example 167) in 1 mL of tetrahydrofuran was added 0.54 mL of 1M LiOH and 0.27 mL methanol. The mixture was stirred at room temperature for 3 hours after which point 0.5 mL of 1N phosphoric acid was added to the solution. The mixture was partitioned between ethyl acetate (3×5 mL) and water (5 mL). The organic layer was washed with saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated. To the residue was added 0.4 mL of hydrochloric acid in dioxane. This solution was stirred at room temperature for 0.5 hour. The solution was then washed with water and concentrated in vacuo, followed by purification by preparative HPLC (gradient of 100:0 0.1% TFA/H2O:acetonitrile to 30:70 0.1% TFA/H2O:acetonitrile) to obtain 16.4 mg of product as the TFA salt. MH+419.3. 1H NMR (DMSO d6, δ): 8.89 (br. s, 1H), 8.63 (s, 1H), 8.57 (d, 1H), 7.88 (dt, 1H), 7.85 (s, 1H), 7.82 (s, 1H), 7.50 (dd, 1H), 7.32 (s, 1H), 7.29 (s, 1H), 6.96 (m, 2H), 6.73 (d, 1H), 6.38 (br. s, 1H), 5.08 (m, 1H), 4.38 (m, 1H), 2.76 (m, 1H), 2.71 (m, 1H), 1.99 (m, 1H), 1.67 (m, 1H).

Provenance & Evidence