1,1-Dimethylethyl N-[1-[2-[(methylsulfonyl)oxy]ethyl]cyclopropyl]carbamate → HCID 12993141, compound

HRID 539967Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9]1)(=O)=O.[C:19]1(=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[NH:20]1.[K]>CN(C)C=O>[O:29]=[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[N:20]1[CH2:6][CH2:7][C:8]1([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-{1-[(tert-butoxycarbonyl)amino]-cyclopropyl}ethyl methanesulfonate (9.5 g, 344.3 mmol) in anhydrous N,N-dimethylformamide (20 ml) was added potassium 2,3-dihydro-1H-isoindole-1,3-dione (7.0 g, 37 mmol). After being stirred at 150° C. for 18 hours, the resulting mixture was then filtered and washed with diethyl ether (50 mL). The filtrate was washed with brine (50 mL×3), dried over sodium sulfate and concentrated in vacuo. The residue was heated with stirring in water and the precipitate was collected by filtration and dried in vacuo to afford 6.0 g of the pure product as an orange solid (yield was 53%).

Workup

filtrationthe resulting mixture was then filtered
washwashed with diethyl ether (50 mL)
washThe filtrate was washed with brine (50 mL×3)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
temperatureThe residue was heated
stirringwith stirring in water
filtrationthe precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-acb793fb3ad64145903c0225ba902c42
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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