Lithium Hydroxide → HCID 25168566, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-5-(4-ethylbenzyl)-2-((2-oxopropoxy)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (36.8 g, 0.057 mmol) (prepared from intermediate J using a Wacker oxidation as described for the preparation of intermediate T-1 below) in THF:MeOH:H2O (2:3:1, 1.2 mL) was added lithium hydroxide (3.71 mg). The reaction was stirred overnight at 20° C. The volatiles were removed and the residue was dissolved in EtOAc (20 mL), washed 1× with brine, 1× with brine containing 2 mL of 5% aqueous KHSO4 and dried over Na2SO4. Concentration gave 16 mg of pure product as a white solid. 1H-NMR (CD3OD, 300 MHz) δ 7.47 (s, 1H), 7.44 (s, 1H), 7.08 (s, 4H), 4.80 (d, J=12.3 Hz, 1H), 4.55 (d, J=9.6 Hz, 1H), 4.22 (s, 2H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.85 (dd, J=11.7 Hz, 2.1 Hz, 1H), 387-3.83 (m, 1H), 3.68-3.63 (m, 1H), 3.50-3.36 (m, 4H), 2.58 (q, J=7.8 Hz, 2H), 2.12 (s, 3H), 1.19 (t, J=7.8 Hz, 3H); LC-MS (m/z) 479 [(M+1)+], 523 [(M+45)−].

Provenance & Evidence