p-Toluenesulfonic acid monohydrate → Ethyl 2-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:25])[N:5]([CH2:12][CH:13]([C:19]1([CH3:24])OCC[O:20]1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]2=[O:11].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:25])[N:5]([CH2:12][CH:13]([C:19](=[O:20])[CH3:24])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]2=[O:11]Participants
3
Procedure
Ethyl 2-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate was prepared (121 mg, 31%) in the same manner as described in the above example 6 (20) from ethyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.46 g, 1.46 mmol) and p-toluenesulfonic acid monohydrate (50 mg), and the obtained product was identified with the following NMR data.
Sources & evidence
- ORD record
- ord-9d97126b1e0d43839371c77736e5d7fa
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094908B2
Reaction notes
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