Ethanol → HCID 68496916, compound
Reaction equation
C(O)C.[CH2:4]([CH:6]1[CH2:15][CH:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([OH:16])[CH2:13]2)[CH2:8][N:7]1[CH2:19][C:20]1[CH:25]=[C:24](OC)[C:23](OC)=[C:22]([O:30][CH3:31])[CH:21]=1)[CH3:5]>C1COCC1.[Pd]>[CH2:4]([CH:6]1[CH2:15][CH:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([OH:16])[CH2:13]2)[CH2:8][N:7]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:30][CH3:31])[CH:21]=1)[CH3:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Pd/C (10%, 30.3 mg), THF (2.0 mL) and ethanol (2.0 mL) were reacted with 263 (292, 0.7 mmol) in THF (4.0 mL) as described for the synthesis of 264. The residue was purified by flash column chromatography using Flashmaster (SiO2: 5 g, hexane 100% to hexane/ethyl acetate 60:40). The title compound was obtained as yellow oil (211 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 0.98 (3H, t, J 7.2, CH2CH3), 1.42 (1H, sept, J 7.1, one of CH2CH3), 1.69 (1H, sept, J 6.8, one of CH2CH3), 2.52 (1H, dd, J 16.4, 6.3, one of ArCH2CH), 2.80 (1H, dd, J 16.4, 5.1, one of ArCH2CH), 2.86-2.90 (1H, m, CHN), 3.58-3.73 (4H, m, 2×ArCH2N), 3.80 (6H, s, 2×OCH3), 6.42 (1H, s, CH), 6.64 (1H, s, CH), 6.79 (1H, dd, J 8.0, 2.2, CH), 6.92-6.98 (2H, m, 2×CH), 7.22 (1H, t, J 7.8, CH). 13C NMR (100 MHz, CDCl3) δ 11.1, 23.0, 29.5, 50.9, 55.0, 55.1, 55.9, 58.5, 108.8, 112.3, 114.1, 114.6, 121.1, 125.3, 126.7, 129.1, 141.5, 143.9, 144.9, 159.6. LC/MS (ES+) tr 1.13 min; m/z 328.10 ((M+H)+, 100%); MeOH/H2O 95:5 (1.0 mL/min), HPLC tr 2.86 min (>99%); CH3CN/H2O 90:10 (1.0 mL/min).
Workup
- customThe residue was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-dab66398ab5240379a7470a6ef1052eb
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394825B2
Reaction notes
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