4-Acetylbenzoic Acid → 2-{5-[3-(4-Carboxy-phenyl)-3-oxo-E-propenyl]-2,4-dimethoxy-phenyl}-pyrrole-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:18]=[C:17]([CH:19]=O)[C:16]([O:21][CH3:22])=[CH:15][C:14]=1[O:23][CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)(=[O:27])[CH3:26]>>[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:18]=[C:17](/[CH:19]=[CH:26]/[C:25]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=2)=[O:27])[C:16]([O:21][CH3:22])=[CH:15][C:14]=1[O:23][CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
The title compound was prepared by condensing 2-(5-formyl-2,4-dimethoxy-phenyl)-pyrrole-1-carboxylic acid tert-butyl ester (Ex-57A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 205–207° C., 6% yield. 1H-NMR (DMSO-d6) δ 8.19 (d, J=5 Hz, 2H), 8.00–8.10 (m, 3H), 7.87 (s, 1H), 7.80 (d, J=16 Hz, 1H), 7.27–7.28 (m, 1H), 6.71 (s, 1H), 6.22–6.23 (m, 1H), 6.14–6.16 (m, 1H), 3.96 (s, 3H), 3.79 (s, 3H), 1.29 (s, 9H). MS m/z=476 ([M−H]+). HMRS (EI) calcd. for C27H27NO7: 477.1788; found: 477.1793.
Sources & evidence
- ORD record
- ord-d609123f72e340f8a6b558bc8f9e3250
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094801B2
Reaction notes
Loading…