Hydrochloric Acid → HCID 59520077, compound

Participants

Reaction Steps

A solution of 3C (120 mg, 0.309 mmol) in 8 mL of 1.6 N NaOH was stirred at rt overnight. The reaction mixture was acidified to pH 2 with 10% HCl and extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to afford the title compound (76 mg) as an orange oil. 1H NMR (CD3OD) δ 1.58 (s, 3H), 1.98-2.04 (m, 1H), 2.13-2.19 (m, 1H), 2.43 (s, 3H), 3.49-3.54 (m, 1H), 3.65-3.70 (m, 1H), 4.12 (t, J=6.1, 1H), 7.59 (d, J=8.3, 1H), 7.65 (d, J=8.8, 1H); 13C NMR (CD3OD) δ 15.33, 23.61, 31.78, 48.13, 74.81, 81.10, 109.72, 117.40, 122.04, 130.98, 132.84, 137.85, 143.90, 175.19; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA; 1 min hold, 4 mL/min UV detection at 220 nm, 2.55 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 2.40 min retention time (89%); MS (ES) m/z 374 [M+H]+.

Provenance & Evidence