alpha-Methylene butyrolactone → 3-(Tert-butoxycarbonyl)-2-methyl-6-((2-oxo-2,5-dihydrofuran-3-yl)methyl)benzyl acetate

HRID 2378610Notes

Reaction equation

C(OC(N[C:9]1[C:10]([CH3:21])=[C:11]([C:17](I)=[CH:18][CH:19]=1)[CH2:12][O:13][C:14](=[O:16])[CH3:15])=O)(C)(C)C.[CH2:22]=[C:23]1[CH2:28][CH2:27][O:26][C:24]1=[O:25].[C:29]([O-:32])(=[O:31])C.[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:13][CH2:12][C:11]1[C:17]([CH2:22][C:23]2[C:24](=[O:25])[O:26][CH2:27][CH:28]=2)=[CH:18][CH:19]=[C:9]([C:29]([O:32][C:10]([CH3:21])([CH3:11])[CH3:9])=[O:31])[C:10]=1[CH3:21])(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

Acetic acid 3-tert-butoxycarbonylamino-6-iodo-2-methyl-benzyl ester (575 mg, 1.4 mmol) was dissolved in N,N-dimethylformamide (2.5 mL). α-Methylene-γ-butyrolactone (190 μL, 2.2 mmol) was added to the mixture followed by potassium acetate (420 mg, 4.3 mmol), and then palladium(II) acetate (16 mg, 0.07 mmol). Reaction mixture was heated at 80° C. for 26 hours. Mixture was cooled to room temperature and partitioned between ethyl acetate and aqueous sodium bicarbonate. Layers were separated. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound as off-white solid in 54% yield. MS m/e (M−H)−=374.

Workup

customReaction mixture
temperatureMixture was cooled to room temperature
custompartitioned between ethyl acetate and aqueous sodium bicarbonate
customLayers were separated
dry with materialOrganic layer was dried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f6b939f3e43144c390dda20970e8bca0
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470679B2

Reaction notes

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