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Thiophenol → (2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-N-(1-cyanocyclopropyl)-4-(phenylthio)pyrrolidine-2-carboxamide

HRID 1697733
ノート
印刷プレビュー

反応式

HRID 1697733 の反応式
C1(S(O[C@H:11]2[CH2:15][C@@H:14]([C:16](=[O:23])[NH:17][C:18]3([C:21]#[N:22])[CH2:20][CH2:19]3)[N:13]([C:24]([C:26]3([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:28][CH2:27]3)=[O:25])[CH2:12]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[C:47]1([SH:53])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CC(N(C)C)=O.O>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2([C:24]([N:13]3[CH2:12][C@H:11]([S:53][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:15][C@H:14]3[C:16]([NH:17][C:18]3([C:21]#[N:22])[CH2:20][CH2:19]3)=[O:23])=[O:25])[CH2:28][CH2:27]2)=[CH:34][CH:33]=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

7

反応物 4

HCID 7969ThiophenolHCID 8028Tetrahydrofuran2 回HCID 11430Potassium CarbonateHCID 86646867(3S,5S)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-5-(1-cyanocyclopropylcarbamoyl)pyrrolidin-3-yl Benzenesulfonate

生成物 1

HCID 67277395(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-N-(1-cyanocyclopropyl)-4-(phenylthio)pyrrolidine-2-carboxamide
収率 101.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
22 °C

実験手順

To a suspension of (3S,5S)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-5-(1-cyanocyclopropylcarbamoyl)pyrrolidin-3-yl benzenesulfonate (example 457c; 200 mg) and potassium carbonate (134 mg) in dimethylacetamide (1 mL) was added at tetrahydrofuran (1.2 mL) at room temperature THF and benzenethiol (50.7 mg). The reaction mixture was stirred at 22° C. for 20 hr then poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The crude mixture was concentrated to dryness and purified by chromatography on silica gel to yield the title compound as a colorless oil (184 mg; 89%). MS (ESI): m/z=466.13 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe crude mixture was concentrated to dryness
  6. custompurified by chromatography on silica gel

出典と根拠

ORDレコード
ord-44de6e0ec5d14a138b9c3166326cfdc1
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163793B2

反応ノート

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