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

HRID 1040480
ノート
印刷プレビュー

反応式

HRID 1040480 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
-40 °C

実験手順

(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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-3bfdbaadbc93402d8fc1b0b8ba32d992
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08552205B2

反応ノート

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