MeOH tetrahydrofuran → HCID 67254837, compound
Reaction equation
[C:1](/[C:3](=[CH:20]\[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH:25]=[CH:24]2)/[C:4]([O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11]OCCOCCOC)=[O:5])#[N:2].C1C[O:40][CH2:39]C1.[CH3:42]O>>[C:1](/[C:3](=[CH:20]\[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([N:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[CH:25]=[CH:24]2)/[C:4]([O:6][CH2:7][CH:8]1[CH2:39][O:40][C:10]([CH3:11])([CH3:42])[O:9]1)=[O:5])#[N:2]Participants
Procedure
Compound 31 (50 mgr, 0.12 mmol) was dissolved in a mixture of THF/MeOH (1:1) and DOWEX-H+ resin (15 mgr) was added and the heterogeneous mixture was stirred for 20 hours. The resin was removed by filtration and triethylamine was added and the solvent was removed under reduced pressure. The residue was purified by flash chromatography to give compound 32. 32: 38 mgr, 84% yield; red liquid; 1H NMR (400 MHz, CDCl3) δ 8.30 (s, 1H), 8.19 (s, 1H), 8.08 (d, 1H, J=8.8 Hz), 7.74 (d, 1H, J=9.1 Hz), 7.63 (d, 1H, J=9.1 Hz), 7.29 (m, 1H), 7.03 (s, 1H), 4.46-4.36 (m, 2H), 4.09 (m, 1H), 3.81 (dd, 1H, J=5.5 Hz, J=11.3 Hz), 3.73 (dd, 1H, J=5.5 Hz, J=11.3 Hz), 3.41 (m, 4H), 1.74-1.67 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 163.6, 156.0, 152.0, 137.9, 135.0, 130.7, 127.3, 126.3, 125.9, 125.5, 119.2, 116.6, 108.3, 97.8, 69.9, 67.0, 63.2, 49.3, 25.5, 24.3; HRMS Calc for C22H25N2O4 (M+H)+ 381.1809 found 381.1802.
Workup
- additionwas added
- customThe resin was removed by filtration and triethylamine
- additionwas added
- customthe solvent was removed under reduced pressure
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-4cd13fda01534584a639ac50bcac1e83
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940918B2
Reaction notes
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