p-Toluenesulfonic acid monohydrate → Methyl 2-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])[N:6]([CH2:13][CH:14]([C:19]1([CH3:24])OCC[O:20]1)[C:15]([O:17][CH3:18])=[O:16])[C:5]2=[O:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[Cl:1])[C:5](=[O:25])[N:6]([CH2:13][CH:14]([C:19](=[O:20])[CH3:24])[C:15]([O:17][CH3:18])=[O:16])[C:7]2=[O:12]Participants
3
Procedure
Methyl 2-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (46 mg, 19%) in the same manner as described in the above example 6 (1) from methyl 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.24 g, 0.67 mmol) and p-toluenesulfonic acid monohydrate (51 mg), and the obtained product was identified with the following NMR data.
Sources & evidence
- ORD record
- ord-65905da7d6be42118321cab77b1401e3
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094908B2
Reaction notes
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