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

HRID 898857노트

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HRID 898857 반응식
[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

참가 물질

4

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

생성물 1

HCID 67524799HCID 67524799, 화합물수율 75%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-b5ef0201819e413983891e5184c5392f
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07351825B2

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