Lithium Hydroxide → HCID 58257042, compound

Participants

Reaction Steps

To a solution of 4 (171 mg, 0.17 mmol, 1 eq) in THF (6 mL) at 0° C. was added a solution of LiOH (6.0 mg, 0.25 mmol, 1.5 eq) in H2O (2 mL) dropwise. The mixture was stirred for 2 h, then quenched with 1N HCl (2 mL) and brine (10 mL). The organic layer was separated and the resulting aqueous layer was further extracted with EtOAc (2×15 mL) and CH2Cl2 (15 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The resulting carboxylic acid was then dried under high vacuum for 2 h, To a solution of MNBA (69 mg, 0.21 mmol, 1.2 eq) and DMAP (49.3 mg, 0.40 mmol, 2.4 eq) in CH2Cl2 (150 mL) was added a solution of the crude carboxylic acid in CH2Cl2 (60 mL) and THF (10 mL) dropwise over 3 h. The reaction mixture was then left to stir at rt overnight. The solvent was then removed in vacuo and the residue was further purified by silica gel column chromatography with hexane/EtOAc (2:3) to yield 5 as a white solid (83 mg, 50%).

Provenance & Evidence