Methanol → HCID 57835786, compound

Participants

Reaction Steps

Compound 30 (0.048 g, 0.11 mmol) was added to a 1-dram vial and dissolved in a minimal amount of anhydrous THF. An aqueous solution of lithium hydroxide (2 M, 0.3 mL) was added to the vial. MeOH was added dropwise until the layers were miscible. The vial was sealed and placed on a rotating wheel overnight (18 hours). When the reaction was complete, the solvent was concentrated under a flow of nitrogen until only water was left. The mixture was diluted by the addition of ˜1 mL of water. Hydrochloric acid (3 N aqueous solution) was added dropwise until the pH reached 2. The aqueous solution was extracted with DCM, and the organic layer was dried and concentrated. Flash column chromatography with 0 to 100% EtOAc/hexanes as the eluant and HPLC of the residue afforded 31 as a white film. MS ESI (pos.) m/e: 407.2 (M+H). 1H NMR (400 MHz) (CDCl3) δ 7.35-7.2 (m, 7H); 7.17 (dd, J=5.1, 1.0 Hz, 1H); 6.93-6.73 (m, 4H); 4.72 (m, 1H); 4.61 (m, 1H); 3.16 (dd, J=15.9, 7.6 Hz, 1H); 3.07 (dd, J=15.9, 7.9); 2.61 (m, 1H); 2.19 (m, 2H); 2.02-1.95 (m, 2H); 1.73-1.61 (m, 4H); 0.91-0.69 (m, 2H).

Provenance & Evidence