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

HRID 1040480
Notes
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Reaction equation

HRID 1040480 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 67117129tert-Butyl (1-(furan-2-yl)cyclopropyl)carbamate

Product 1

HCID 67390395[1-(5-Cyano-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

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

  1. additionChloroulfonyl isocyante (0.45 mL, 5.1 mmol) was added in one portion via syringe
  2. stirringstirring
  3. waitcontinued at room temperature for 30 min
  4. extractionextracted with EtOAc (3×50 mL)
  5. concentrationThe combined organic layers were concentrated to a red liquid
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes