Hydrochloric Acid → 17-[2-(4-Isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

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Reaction Steps

To a solution of 17-[2-(4-isopropyl-thiazol-2-yl)-7-methoxy-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester (34, 182 mg, 0.275 mmol) in dioxane (3 mL) and MeOH (1.5 mL) was added a 1 M aqueous solution of LiOH (3 mL). After 72 h, the reaction mixture was successively acidified to pH 2 with 1.7 M HCl and evaporated under vacuum. Then, 1 g of silica was added towards the end to adsorb the crude product. Purification by flash column chromatography (15 g YMC silica; gradient MeOH/CH2Cl2: 200 mL each 2%, 4%, 6%, 100 mL each 8%, 10%; forefraction 100 mL followed by 15-mL fractions, desired product fractions 33-42) gave 164 mg (94%) of the title product 35 as a yellow solid: Rf (10% MeOH—CH2Cl2)=0.38.

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