5-[5-(Trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonyl chloride → HCID 67524799、化合物

HRID 898857ノート

反応式

HRID 898857 の反応式
[NH2:1][C@:2]12[C@@H:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C@H:6]1[CH2:5][O:4][C:3]2=[O:14].[F:15][C:16]([F:32])([F:31])[C:17]1[O:21][N:20]=[C:19]([C:22]2[S:26][C:25]([S:27](Cl)(=[O:29])=[O:28])=[CH:24][CH:23]=2)[CH:18]=1>N1C=CC=CC=1>[O:14]=[C:3]1[O:4][CH2:5][C@H:6]2[C@:2]1([NH:1][S:27]([C:25]1[S:26][C:22]([C:19]3[CH:18]=[C:17]([C:16]([F:15])([F:31])[F:32])[O:21][N:20]=3)=[CH:23][CH:24]=1)(=[O:28])=[O:29])[C@H:7]2[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 27775265-[5-(Trifluoromethyl)-1,2-oxazol-3-yl]thiophene-2-sulfonyl chlorideHCID 67524225HCID 67524225、化合物

生成物 1

HCID 67524799HCID 67524799、化合物収率 75%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

(1R*,5R*,6R*)-1-amino-6-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one (0.14 g, 0.74 mmol) was dissolved in 3 mL of pyridine. After cooling to 0° C., 5-(5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-sulfonyl chloride (0.31 g, 0.96 mmol) was added in one portion. The reaction mixture was warmed to room temperature and stirred overnight. After concentration, the reaction mixture was diluted with EtOAc, washed with 10% citric acid, water (×2), 5% NaHCO3 and brine and dried over Na2SO4. After concentration, the crude product was purified by column chromatography using 2:1 hexanes/EtOAc to afford 0.26 g (75%) of the desired product.

後処理

  1. temperatureThe reaction mixture was warmed to room temperature
  2. concentrationAfter concentration
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with 10% citric acid, water (×2), 5% NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-b5ef0201819e413983891e5184c5392f
出典データセット
uspto-grants-2008_04
特許番号
US07351825B2

反応ノート

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