1,1'-Carbonyldiimidazole → 3-(4-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[N:11]([CH:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:20]=3)[CH2:15][C:16]([OH:18])=O)[C:9](=[O:10])[C:8]2=[CH:33][CH:34]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:48][OH:49]>O1CCCC1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[N:11]([CH:14]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH:20]=3)[CH2:15][C:16]([NH:48][OH:49])=[O:18])[C:9](=[O:10])[C:8]2=[CH:33][CH:34]=1)(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(4-Acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(4-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid (1.78 g, 3.82 mmol), carbonyldiimidazole (0.74 g, 4.6 mmol) and hydroxylamine hydrochloride (0.38 g, 5.3 mmol) in tetrahydrofuran (12 mL) to afford 3-(4-acetoamidophthalimido)-3-(3-cyclopentyloxy-4-methoxyphenyl)-N-hydroxypropionamide as a white solid (1.1 g, 60% yield): mp, 177–180° C.; 1H NMR (DMSO-d6) δ 1.87–1.56 (m, 8H, C5H8), 2.12 (s, 3H, CH3), 3.11 (d, J=7.5 Hz, 2H, CH2), 3.70 (s, 3H, CH3), 4.72 (m, 1H, OCH), 5.64 (t, J=7.5 Hz, 1H, NCH), 6.88 (br s, 2H, Ar), 7.01 (br s, 1H, Ar), 7.81 (m, 2H, Ar), 8.17 (br s, 1H, OH), 8.78 (s, 1H, Ar), 10.56 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 21.13, 21.81, 29.79, 31.89, 47.78, 53.15, 77.18, 109.68, 110.16, 111.75, 117.29, 120.85, 121.95, 122.40, 128.89, 131.50, 142.48, 144.33, 163.63, 165.20, 165.50, 166.92; Anal Calcd for C25H27N3O7+1.2 H2O: C, 59.68; H, 5.89; N, 8.35. Found: C, 59.69; H, 8.19; H2O, 6.91.
Sources & evidence
- ORD record
- ord-5cfb528261ed466e95bdfc3e1d9282d0
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091356B2
Reaction notes
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