Hydrochloric Acid → HCID 21084006, 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(OCC)=O)[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.Cl>O1CCOCC1>[O:1]1[CH2:2][CH2:3][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:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:24][S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:5][CH2:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The compound of Example 92 (91 mg, 0.18 mmol) was dissolved in dioxane (1 mL) and 4M HCl(aq) (1 mL) added and the mixture heated at reflux for 48 h. The reaction was partitioned between 2M NaOH(aq) and THF and the combined THF layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0–10% MeOH in EtOAc) to give the title compound as an off-white solid (73 mg, 94%). δH (CDCl3) 7.74 (1H, d, J 9.6 Hz), 7.33–7.28 (7H, m), 7.05–7.01 (2H, m), 6.75 (1H, s), 6.58 (1H, d, J 9.6 Hz), 4.12 (2H, t, J 5.7 Hz), 3.76–3.67 (4H), m), 2.78 (2H, t, J 5.7 Hz), 2.56–2.52 (4H, m). LCMS (ES+) RT 2.46 minutes, 433 (M+H)+.