Triethylamine → 3-(4-Difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]([NH2:19])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([F:15])[F:14])=[C:8]([O:16][CH2:17][CH3:18])[CH:7]=1.C([O:23][C:24](=O)[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:34]Br)C.C(N(CC)CC)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([F:14])[F:15])=[C:8]([O:16][CH2:17][CH3:18])[CH:7]=1)[N:19]1[CH2:34][C:26]2[C:25](=[C:30]([N+:31]([O-:33])=[O:32])[CH:29]=[CH:28][CH:27]=2)[C:24]1=[O:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(4-Difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester was prepared by the procedure of example 11 from 3-amino-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester (7.3 g, 0.025 mol), 2-bromomethyl-6-nitro-benzoic acid ethyl ester (7.6 g, 0.028 mol) and triethyl amine (7 ml, 0.05 mol) in DMF (50 ml) to provide 3-(4-difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester as yellow oil (9.1 g, 81% yield). 1H NMR (CDCl3): δ 1.42 (t, J=7.5 Hz, 3H, OCH2CH3), 3.09 (dd, J=6.8, 15 Hz, 2H, CH2CO), 3.29 (dd, J=6.8, 15 Hz, 1H, CH2CO), 3.65 (s, 3H, OCH3), 4.10 (q, J=7.5 Hz, 2H, OCH2CH3), 4.26 (d, J=17 Hz, 2H, CH2N), 4.46 (d, J=17 Hz, 2H, CH2N), 5.80-5.86 (m, 1H, CHN), 6.55 (t, JH-F=75 Hz, 1H, OCF2H), 6.92 (dd, J=1.8, 8.2 Hz, 1H, Ar), 7.06 (d, J=1.8 Hz, 1H, Ar), 7.14 (d, J=8.25, 1H, Ar), 7.58-7.76 (m, 3H, Ar).
Sources & evidence
- ORD record
- ord-a667f61d6de44e47ba4dbe0f093a45f1
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504427B2
Reaction notes
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