Lithium Hydroxide → HCID 89455725, compound

Participants

Reaction Steps

To a solution of methyl 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoate (2.260 g, 6.29 mmol) in THF (25 ml), aqueous 1M LiOH (6.29 ml, 6.29 mmol) was added, and the reaction was stirred at RT for 6 hours. Additional 1M LiOH (12.58 ml, 12.58 mmol) was added over 3 days with stirring at the same temperature. The solvents were removed under vacuum, and the residue was partitioned between EtOAc and 2N HCl; the organic phase was dried over Na2SO4 and the solvent was removed. The crude was purified by chromatography on silica gel column (DCM:MeOH=98:2 to 9:1) to afford 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoic acid (1.240 g, 3.59 mmol, 57.1% yield, MS/ESI+ 368.0 [MHNa]+).

Provenance & Evidence