Toluene-p-sulphonic anhydride → Allyl 2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-3-oxo-butyrate

HRID 10899

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:26])[N:5]([CH2:12][CH:13]([C:20]1([CH3:25])OCC[O:21]1)[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[C:6]2=[O:11].C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>CC(C)=O.O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:26])[N:5]([CH2:12][CH:13]([C:20](=[O:21])[CH3:25])[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[C:6]2=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Allyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (331 mg, 0.91 mmol) was dissolved in a a solvent mixture of acetone/water (v/v=5/1), and catalyst amount of p-toluenesulfonic acid anhydride was added to the obtained solution. The resulting mixture was refluxed at 80° C. for 18 hours. After the reaction was completed, the reaction mixture was washed with water, and then acetone was removed by distilling under a reduced pressure. The residue was extracted with dichloromethane. The combined organic layer was dried with anhydrous sulfate and distilled under a reduced pressure. The desired product was obtained (131.2 mg, 31%) by performing column chromatography (eluent: n-hexane/ethyl acetate=2/1).

Workup

additionwas added to the obtained solution
washthe reaction mixture was washed with water
customacetone was removed
distillationby distilling under a reduced pressure
extractionThe residue 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-dbb505f7b1a54d5491bd553456441248
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094908B2

Linked notes

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