Lithium hydroxide, monohydrate → 7-((3-(tert-Butoxycarbonyl)azetidin-1-yl)methyl)-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylic acid

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Reaction Steps

A mixture of methyl 7-((3-(tert-butoxycarbonyl)azetidin-1-yl)methyl)-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate (Preparation 45D, 95 mg, 0.238 mmol) and lithium hydroxide monohydrate (12.01 mg, 0.286 mmol) in THF (3 mL) and water (1.500 mL) was allowed to stir at room temperature overnight. The THF was evaporated and the residue diluted with 5 ml of water. The pH was adjusted to 5-6 and extracted with ethyl acetate six times. The organic layers were combined, dried over sodium sulfate and concentrated to afford 110 mg of product (HPLC purity 75-80%). The compound had an HPLC ret. time=0.67/2.0 min. (condition E); MS:(M+H)=385.3.

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