Sodium Hydroxide → HCID 23653902, compound

Participants

Reaction Steps

150 mg of 15 (280 μmol) in 1,4 ml of THF and 2.78 ml of 1N hydrochloric acid are introduced into a 20 ml round-bottomed flask, with stirring and under argon. The stirring is maintained for 4 h at AT. The medium is neutralized with NaOH (1N), to pH 7, and extracted with 2 times 5 ml of EtOAc. The combined organic phases are dried over MgSO4, filtered and evaporated to dryness. The crude is chromatographed on a silica cartridge (10 g) with an eluent of CH2Cl2/MeOH (as an MeOH gradient of 1 to 10%). 85 mg of expected product Ex4 are recovered. 58 mg of Ex4 are separated by preparative chiral HPLC (Chirapad AD-H 5 μm 250×4.6 mm, flow rate 1 ml/min, mobile phase: 70% heptane-30% EtOH, 0.1% TEA), to give 16 mg of Ex4a (tr=13.42 min) and 40 mg of Ex4b (tr=18.96 min).

Provenance & Evidence