N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolane-4-ylidene)-N-methoxy-acetamide → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1h-pyrrole-3-carboxylic acid (3,4-dichlorobenzyl)-methoxy-amide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]([O:18][CH3:19])[C:7](=[O:17])[CH:8]=[C:9]1[C:13](=[O:14])OC(C)(C)[O:10]1.[CH2:24]=O.[NH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]([O:18][CH3:19])[C:7]([C:8]1[CH2:24][N:26]([CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[C:13](=[O:14])[C:9]=1[OH:10])=[O:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Reaction of N-(3,4-dichlorobenzyl)-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-acetamide (0.20 g, 0.56 mmol) with the paraformaldehyde-N-(2-aminoethyl)morpholine adduct in methanol using a procedure similar to the one described in the preparation of compound 13 gave 0.071 g (28% yield) of the title compound as a solid after chromatography on reversed phase silica gel. 1HNMR 400 MHz (DMSO-d6) δ (ppm); 2.39 (4H, broad, 2×NCH2), 2.47 (2H, t, J=6.3 Hz, NCH2), 3.49 (2H, t, J=6.3 Hz, NCH2), 3.53 (4H, broad, 2×OCH2), 3.66 (3H, s, OCH3), 4.16 (2H, s, NCH2), 4.89 (2H, s, NCH2), 7.33 (1H, dd, J=1.8 Hz and J=8.1 Hz, aromatic), 7.60 (1H, d, J=8.1 Hz, aromatic), 7.63 (1H, d, J=1.8 Hz, aromatic). HRMS (MAB/N2) calculated for C19H23C2N3O5: [M+]: 443.101477. found: 443.103002.
Sources & evidence
- ORD record
- ord-c76b23e6ab374ea6b1c117b217bc788b
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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