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

HRID 1040480
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HRID 1040480 반응식
[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]
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5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

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온도
-40 °C

실험 절차

(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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-3bfdbaadbc93402d8fc1b0b8ba32d992
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552205B2

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