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tert-Butyl 4-carbamothioylpiperidine-1-carboxylate → 4-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]piperidine

HRID 1916441
ノート
印刷プレビュー

反応式

HRID 1916441 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:18][C:19]([C:21]1[CH2:25][CH:24]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[O:23][N:22]=1)=O>CC(C)=O>[F:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[CH:24]1[O:23][N:22]=[C:21]([C:19]2[N:15]=[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[S:16][CH:18]=2)[CH2:25]1
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

4

反応物 2

HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 866575632-Bromo-1-(4,5-dihydro-5-(2,6-difluorophenyl)-3-isoxazolyl)ethanone2 回

生成物 1

HCID 666185904-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]piperidine

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
45 °C

実験手順

A mixture of 1-tert-butoxycarbonylpiperidine-4-carbothioamide (7.33 g, 30 mmol) and 2-bromo-1-(4,5-dihydro-5-(2,6-difluorophenyl)-3-isoxazolyl)ethanone (i.e. the product of Step C) (9.12 g, 30 mmol) in acetone (100 mL) was heated at 45° C. for 3 h, and then stirred at room temperature overnight. The reaction mixture was concentrated, and the resulting residue was dissolved in dichloromethane (100 mL) and trifluoroacetic acid (40 mL), stirred at room temperature for 3 h and then concentrated under reduced pressure. The resulting oil was dissolved in aqueous hydrochloric acid solution (0.5 N, 200 mL) and extracted with ethyl acetate. The organic layer was basified by adding aqueous sodium hydroxide solution (10% in water), then washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a thick amber-colored oil (8.62 g, weight included residual ethyl acetate).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe resulting residue was dissolved in dichloromethane (100 mL)
  3. stirringtrifluoroacetic acid (40 mL), stirred at room temperature for 3 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting oil was dissolved in aqueous hydrochloric acid solution (0.5 N, 200 mL)
  6. extractionextracted with ethyl acetate
  7. additionby adding aqueous sodium hydroxide solution (10% in water)
  8. washwashed with saturated aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-823fd18bce7d42428dd41ea013c778d0
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08618137B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート