1,1'-Carbonyldiimidazole → N-hydroxy-3-{3-(2-propoxy)-4-methoxyphenyl}-3-phthalimidopropionamide
Reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:13]([N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])[CH2:14][C:15](O)=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:42][OH:43]>O1CCCC1>[OH:43][NH:42][C:15](=[O:16])[CH2:14][CH:13]([C:7]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:6]=1)[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N-Hydroxy-3-{3-(2-propoxy)-4-methoxyphenyl}-3-phthalimidopropionamide was prepared by the procedure of Example 1 from 3-{3-(2-propoxy)-4-methoxyphenyl}-3-phthalimidopropanoic acid (2.0 g, 5.2 mmol), carbonyldiimidazole (1.02 g, 6.29 mmol), and hydroxylamine hydrochloride (481 mg, 6.92 mmol) in tetrahydrofuran (10 mL) to afford N-hydroxy-3-{3-(2-propoxy)-4-methoxyphenyl}-3-phthalimidopropionamide as a white solid (1.42 g, 68% yield): mp, 119.0–121.0° C.; 1H NMR (DMSO-d6) δ 1.24 (d, J=6.0 Hz, 3H, CH3), 1.243 (d, J=6.0 Hz, 3H, CH3), 3.12 (d, J=7.9 Hz, 2H, CH2), 3.71 (s, 3H, CH3), 4.45–4.51 (m, 1H, CH), 5.68 (t, J=7.9 Hz, 1H, NCH), 6.91 (br s, 2H, Ar), 7.05 (br s, 1H, Ar), 7.84–7.86 (m, 4H, Ar), 8.79 (br s, 1H, OH), 10.60 (1H, NH); 13C NMR (DMSO-d6) δ 21.80, 21.88, 34.19, 50.13, 55.49, 70.44, 112.18, 114.97, 120.12, 123.11, 131.13, 131.21, 134.59, 146.37, 149.51, 165.99, 167.62; Anal Calcd for C21H22N2O6 0.9 H2O: C, 60.83; H, 5.79; N, 6.76. Found: C, 60.83; H, 5.73; N, 6.56; H2O, 4.02.
Sources & evidence
- ORD record
- ord-a1e63243c4814197b9a17347d5a3368b
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091356B2
Reaction notes
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