Pyridine → Ethyl 2-(4-acetoxy-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].N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33]>ClCCl>[C:32]([O: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])(=[O:34])[CH3:33]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 3-(4-hydroxy-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (102.4 mg, 0.34 mmol) was dissolved in dichloromethane, and pyridine (55 μl, 0.682 mmol) and acetyl chloride (49 μl, 0.68 mmol) were then slowly added dropwise to the obtained solution at 0° C. The resulting mixture was then stirred at the same temperature for 10 minutes. After the reaction was completed, the reaction mixture was washed with water and then the aqueous layer was extracted with dichloromethane. The combined organic layer was dried with anhydrous sulfate and distilled under a reduced pressure. The desired product (64 mg, 54%) was obtained by performing column chromatography (eluent: n-hexane/ethyl acetate=3/1).
Workup
- washthe reaction mixture was washed with water
- extractionthe aqueous layer was extracted with dichloromethane
- dry with materialThe combined organic layer was dried with anhydrous sulfate
- distillationdistilled under a reduced pressure
Sources & evidence
- ORD record
- ord-8ab64c3ee79f4ec68259b9f3e101f5c1
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094908B2
Reaction notes
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