Lithium hydroxide, monohydrate → HCID 86628124, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,3S)-methyl 3-(3-(benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)cyclopentanecarboxylate 42 (303 mg, 589 μmol) in 8:1 MeOH/H2O (18 ml) was added lithium hydroxide hydrate (49.5 mg, 1180 μmol). The reaction mixture was stirred for overnight at 55° C. Volatiles were removed by concentration under reduced pressure. The leftover residue was treated with 10 mL water and 10 mL of aqueous 10% HCl. A precipitate formed upon addition of the acid. After standing for 10 min the precipitate was filtered and washed with copious of amounts of water. After drying under vacuum, the precipitate was purified by injection as a solution in DMF on a reverse phase HPLC column using 5->95% CH3CN/0.1% aqueous TFA as eluant. Product 43 was isolated as white solid (250 mg). LCMS (ES) calcd for C29H29N3O3S 499.2 found 500.2 (MH+).

Provenance & Evidence