Potassium Hydroxide → HCID 19029198, compound

Participants

Reaction Steps

A 95% EtOH solution (150 mL) of 17 (5.00 g, 23.6 mmol) and KOH (3.00 g, 53.5 mmol) was stirred at room temperature (48 h). The solvent was removed and the residue was dissolved in H2O (50 mL). The aqueous solution was washed with Et2O (3×50 mL) and then acidified to pH 1.5 with 10% H3PO4. The acidified solution was extracted with EtOAc (3×200 mL) and the combined extracts were dried (Na2SO4), and concentrated in vacuo to give 2.90 g (62%) of 18: mp 178°-180° C. (d) (recrystallized from CH3CN); IR (KBr) 3400 (br), 1700 (br) cm-1 ; 1H NMR (DMSO-d6) δ 1.67 (s, CH3), 1.83 (s, C(O)CH3), 6.39 (m, C3H, C4H), 7.59 (s, C5H), 8.34 (s, NH), 12.63 (s, C(O)OH); 13C NMR (DMSO-d6) 22.20 (C(O)CH3), 22.59 (CH3), 57.65 (C(CH3)), 107.09 (C4), 110.49 (C3), 142.33 (C5), 153.36 (C2), 168.86 (C(O)NH), 171.78 (C(O)OH) ppm; mass spectrum, m/e (relative intensity) 198 (M+ +1, 4), 143 (97), 152 (63), 140 (23), 111 (73), 110 (100), 94 (24). Anal. (C9H11NO4) C, H, N.

Provenance & Evidence