Tetrabutylammonium Hydroxide → HCID 178525569, compound

Participants

Reaction Steps

To a 1,4-dioxane (20 mL) mixture of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-methoxycarbonylmethyl-cyclohexyl ester (1.48 g) obtained in Example 1, tetrabutylammonium hydroxide (1.0 mol/L aqueous solution, 4.0 mL) was added at room temperature. The reaction mixture was stirred for 22 hours and concentrated. The residue was acidified with a 1N aqueous hydrochloric acid solution (30 mL), then diluted with ethyl acetate, and vigorously stirred until complete dissolution. The separated organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated. The residue was purified by chromatography (dichloromethane/methanol). The obtained solid was recrystallized (isopropyl alcohol) to obtain the title compound (1.04 g, 72%) as a white solid.

Provenance & Evidence