Hydrochloric Acid → HCID 42636430, compound

Participants

Reaction Steps

To a solution of (1S,2R,3R,4S,5R,6R)-4-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)cyclohexane-1,2,3,5-tetrayl tetraacetate (38) (300 mg, 47.6 μmol) in MeOH (5 mL) was added sodium hydroxide (29 mg, 72 μmol) and stirred for 1.5 h under reflux. The mixture was acidified to pH 6 with 1 N hydrochloric acid and the solvents were removed under reduced pressure. The residue was purified by preparative HPLC to provide 30 mg of the desired compound. 1H-NMR (400 MHz, CD3OD): δ 7.90 (2H, d, J=8.4 Hz), 7.35 (3H, m), 7.22 (H, d, J=1.6 Hz), 7.18 (1H, d, J=8.4, 1.6 Hz), 4.17 (2H, s), 3.91 (2H, d, J=3.2 Hz), 3.66 (1H, t, J=10.4 Hz), 3.49-3.40 (2H, m), 3.30 (1H, m), 2.57-2.52 (4H, m), 1.55-1.50 (1H, m); MS (ESI+): 421 [M+H]+, 443 [M+Na]+, (ESI−): 465 [M+HCOO]−.

Provenance & Evidence