1,1'-Carbonyldiimidazole → 3-(3-ethoxy-4-methoxyphenyl)-3-(3,6-difluorophthalimido)-N-hydroxypropionamide
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:17]2[C:21](=[O:22])[C:20]3=[C:23]([F:28])[CH:24]=[CH:25][C:26]([F:27])=[C:19]3[C:18]2=[O:29])[CH2:13][C:14](O)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:43][OH:44]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:17]2[C:21](=[O:22])[C:20]3=[C:23]([F:28])[CH:24]=[CH:25][C:26]([F:27])=[C:19]3[C:18]2=[O:29])[CH2:13][C:14]([NH:43][OH:44])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(3-Ethoxy-4-methoxyphenyl)-3-(3,6-difluorophthalimido)-N-hydroxypropionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3,6-difluorophthalimido)propanoic acid (580 mg, 1.43 mmol), carbonyldiimidazole (255 mg, 1.57 mmol) and hydroxylamine hydrochloride (120 mg, 1.73 mmol) in tetrahydrofuran (8 mL) to afford 3-(3-ethoxy-4-methoxyphenyl)-3-(3,6-difluorophthalimido)-N-hydroxypropionamide as a white solid (340 mg, 57% yield): mp, 171.0–172.0° C.; 1H NMR (DMSO-d6) δ 1.32 (t, J=6.9 Hz, 3H, CH3), 3.03 (dd, J=7.9, 14.8 Hz, 1H, CHH), 3.16 (dd, J=8.1, 14.9 Hz, 1H, CHH), 3.71 (s, 3H, CH3), 3.91 (q, J=6.9 Hz, 2H, CH2), 5.62 (t, J=7.8 Hz, 1H, NCH), 6.878–6.95 (m, 2H, Ar), 6.99 (br s, 1H, Ar), 7.74 (t, JH−F=5.8 Hz, 2H, Ar), 8.81 (br s, 1H, OH), 10.61 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 14.64, 33.88, 50.29, 55.44, 63.71, 111.64, 112.44, 118.02 (t, JC-F=9.2 Hz), 119.77, 125.47 (t, JC-F=15 Hz), 130.42, 147.65, 148.59, 152.93 (dd, JC-F=4.2, 261 Hz), 163.49, 165.84; Anal Calcd for C20H18N2O6F2: C, 57.14; H, 4.32; N, 6.66. Found: C, 56.93; H, 4.37; N, 6.31.
Sources & evidence
- ORD record
- ord-0d250504239546bd8125a5af3702c54d
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091356B2
Reaction notes
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