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

HRID 132188Notes

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-1afc1224460a4984ab72fe2825ec23a5
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384930B2

Reaction notes

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