Dimethylformamide → [1-(5-Cyano-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

HRID 1040480Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18](C=O)C>CC#N.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([C:11]2[O:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -40 °C

Procedure

(1-Furan-2-yl-cyclopropyl)-carbamic acid tert-butyl ester (765 mg, 3.43 mmol) was dissolved in MeCN (7.7 mL) and cooled to −40° C. in an acetone/dry ice bath. Chloroulfonyl isocyante (0.45 mL, 5.1 mmol) was added in one portion via syringe and the reaction was allowed to stir at a temperature between −40 and −30° C. for 45 min. Anhydrous DMF (1.2 mL) was then added and stirring continued at room temperature for 30 min. The reaction was diluted with saturated aqueous NaHCO3 (100 ml) and extracted with EtOAc (3×50 mL). The combined organic layers were concentrated to a red liquid and chromatographed (silica, 5→25% EtOAc/hexanes) to give 400 mg of the title compound as a white solid, m/z 234.35 [M-t-Bu+MeCN]+.

Workup

additionChloroulfonyl isocyante (0.45 mL, 5.1 mmol) was added in one portion via syringe
stirringstirring
waitcontinued at room temperature for 30 min
extractionextracted with EtOAc (3×50 mL)
concentrationThe combined organic layers were concentrated to a red liquid
customchromatographed (silica, 5→25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-3bfdbaadbc93402d8fc1b0b8ba32d992
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552205B2

Reaction notes

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