Potassium Hydroxide → HCID 25168702, compound

Participants

Reaction Steps

To a solution of (2S,3R,4R,5S,6R)-2-(4-chloro-2-((2,3-dibromopropoxy)methyl)-5-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (53.3 mg, 0.086 mmol) (prepared by bromination of compound I) in anhydrous ethanol (1.0 mL) was added potassium hydroxide (10.6 mg). The reaction mixture was refluxed and monitored by LC-MS. After 6 h, LC-MS showed the reaction was complete. The reaction mixture was concentrated and the residue was partitioned between EtOAc and water, the organic layer was separated, washed 2× with 1N HCl, 3× with brine, and dried over Na2SO4. Concentration gave the crude product, which was purified by preparative HPLC to yield 21 mg of title compound as a white solid. 1H-NMR (CD3OD, 400 MHz) δ 7.48 (s, 1H), 7.42 (s, 1H), 7.11 (s, 4H), 4.85 (d, J=12.0 Hz, 1H), 4.62 (d, J=12.0 Hz, 1H), 4.51 (d, J=9.2 Hz, 1H), 4.23 (s, 2H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.88 (d, J=12.4 Hz, 1H), 3.71-3.67 (m, 1H), 3.52-3.41 (m, 4H), 2.94 (s, 1H), 2.60 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); LC-MS (m/z) 461 [(M+1)+], 515 [(M+45)−].

Provenance & Evidence