Hydrochloric Acid → HCID 11258796, compound
Reaction equation
C(O[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]3[CH:29]4[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]4)[CH2:25]3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)N)=O)(C)(C)C.[C:32]1([C:38](=O)CC)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl.[CH3:43]CO>>[CH3:43][C:6]1[NH:8][C:10]2[C:11]([C:38]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:12][C:13]([O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH:24]3[CH:29]4[CH2:28][CH2:27][N:26]([CH2:31][CH2:30]4)[CH2:25]3)=[CH:19][CH:18]=1)=[CH:14][CH:15]=2Participants
Procedure
The product of Example 39A (105 mg, 0.25 mmol) was treated with 1-phenyl-propan-1-one (Aldrich, 67 mg, 0.5 mmol) and HCl (Aldrich, 4 M in dioxane, 0.5 mL, 2 mmol) in EtOH (3.0 mL) at 80° C. for 10 h. The mixture was concentrated and the title compound was was purified by preparative HPLC (Xterra™, column, Xterra RP-18 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10) (v. 40/60 to 70/30 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (60 mg, yield, 57%). 1H NMR (300 MHz, CD3OD) δ 1.45–1.80 (m, 4H), 2.09–2.19 (m, 1H), 2.37 (s, 3H), 2.62–2.97 (m, 4H), 3.19–3.44 (m, 1H), 4.34–4.53 (m, 1H), 6.81 (dd, J=8.6, 2.2 Hz, 1H), 6.85–7.04 (m, 4H), 7.09 (d, J=2.4 Hz, 1H), 7.27–7.38 (m, 2H), 7.46 (t, J=7.6 Hz, 2H), 7.63 (d, J=7.1 Hz, 2H) ppm; MS (DCl/NH3) m/z 425 (M+H)+.
Workup
- concentrationThe mixture was concentrated
- customthe title compound was was purified by preparative HPLC (Xterra™, column, Xterra RP-18 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10) (v. 40/60 to 70/30 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (60 mg, yield, 57%)
Sources & evidence
- ORD record
- ord-c88f136bb4c14189bf3e2ad6ecad3735
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241773B2
Reaction notes
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