1-Hydroxybenzotriazole → HCID 90149508, compound

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Reaction Steps

A solution of (S)-2-(((benzyloxy)carbonyl)amino)-8-(tert-butoxy)-8-oxooctanoic acid (prepared as described in WO2006/061638), N-ethyl-N′-(3-dimethylaminopropyl)-carbo diimide hydrochloride (1.3 eq.) and HOBt (1.3 eq.) were dissolved in anhydrous DMF and stirred for 15 min. The resulting solution was added to a mixture of 2-hydroxy-1-(2-methoxyquinolin-3-yl)ethanone (1 eq.) (prepared as described in J. Med. Chem. 2009, 59, 3453-3456) and DMAP (0.3 eq.) in anhydrous DMF (0.7 M). After stirring at room temperature for 16 h the mixture was partitioned between DCM and water. The organic phase was washed with water and brine and dried over Na2SO4. Concentration under reduced pressure gave an oily crude which was used as such. A solution of the resulting oil and ammonium acetate (20 eq.) in xylene was heated under Dean-Stark conditions for 1.5 h. After cooling to room temperature the mixture was diluted with EtOAc and water. The organic phase was separated and washed with sat. aq. NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure to give a crude that was purified by column chromatography (eluent: petroleum ether/EtOAc from 7:3 to 2:3) to give the title compound as a yellow powder. MS (ES+) C32H38N4O5: 559 (M+H)+.

Provenance & Evidence