Ethanol → HCID 21084005, compound

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:24]([C:26]([O:28]CC)=[O:27])[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[OH-].[Na+].CCO>O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[C:24]([C:26]([OH:28])=[O:27])[S:25][C:17]3=4)=[CH:14][CH:15]=2)[CH2:5][CH2:6]1

Participants

Procedure

A mixture of the compound of Example 92 (230 mg, 0.46 mmol), sodium hydroxide (91 mg, 2.28 mmol) and EtOH (5 mL) was heated at reflux for 18 h. EtOH was removed in vacuo and the residue treated with 2M HCl(aq) (2 mL) to give a white solid. The reaction was diluted with water and then freeze dried. The resultant solid was extracted with isopropanol and the extracts concentrated in vacuo to give the title compound as a white solid (97 mg). δH (DMSO-d6) 7.62–7.37 (8H, m), 7.21–7.16 (2H, m), 6.50 (1H, J 9.6 Hz), 4.20 (2H, t, J 5.7 Hz), 3.62–3.59 (4H, m), 2.76 (2H, t, J 5.7 Hz), 2.54–2.51 (4H, m). LCMS (ES+) RT 2.35 minutes, 477 (M+H)+.