3-Fluorophthalic anhydride → Allyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

HRID 10869

Reaction equation

[NH2:1][CH2:2][CH:3]([C:10]1([CH3:15])[O:14][CH2:13][CH2:12][O:11]1)[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5].[F:16][C:17]1[CH:27]=[CH:26][CH:25]=[C:19]2[C:20]([O:22][C:23](=O)[C:18]=12)=[O:21]>C(Cl)(Cl)Cl>[F:16][C:17]1[CH:27]=[CH:26][CH:25]=[C:19]2[C:18]=1[C:23](=[O:22])[N:1]([CH2:2][CH:3]([C:10]1([CH3:15])[O:11][CH2:12][CH2:13][O:14]1)[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])[C:20]2=[O:21]

Participants

Conditions

Temperature: 80 °C

Procedure

Allyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (400 mg, 1.86 mmol) was dissolved in 10 mL of chloroform, and 3-fluorophthalic anhydride (401 mg, 2.42 mol) was added to the obtained solution. The resulting mixture was then refluxed at 80° C. for 3 days after adding. After the reaction was completed, the solvent was evaporated by distilling under a reduced pressure. The residue was purified by performing column chromatography (eluent: n-hexane/ethyl acetate=3/1) to obtain the desired product as a white solid (351 mg, 52%). Rf=0.29 (eluent: n-hexane/ethyl acetate=2/1)

Workup

additionafter adding
customthe solvent was evaporated
distillationby distilling under a reduced pressure
customThe residue was purified

Sources & evidence

ORD record: ord-f8a25e85c5804342b5d24a98cbc5cbf2
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094908B2

Linked notes

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