p-Toluenesulfonic acid monohydrate → Ethyl 2-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]2[C:3]=1[C:4](=[O:26])[N:5]([CH2:13][CH:14]([C:20]1([CH3:25])OCC[O:21]1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]2=[O:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]2[C:7]=1[C:6](=[O:12])[N:5]([CH2:13][CH:14]([C:20](=[O:21])[CH3:25])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]2=[O:26]Participants
3
Procedure
Ethyl 2-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (264 mg, 26%) in the same manner as described in the above example 6 (20) from ethyl 3-(4,7-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (1.13 g, 2.80 mmol) and p-toluenesulfonic acid monohydrate (100 mg), and the obtained product was identified with the following NMR data.
Sources & evidence
- ORD record
- ord-eb0f56ce48264298a0ac8f210ad7cd89
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094908B2
Reaction notes
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