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Water → Trifluoroacetic acid

HRID 70710
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HRID 70710 반응식
CS(O)(=O)=O.[CH:6]1([S:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:28])[C:17]3[NH:22][C:21](=[O:23])[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:7]1.[OH2:29].[CH:30]1([OH:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[F:25][C:24]([F:27])([F:26])[C:20]([OH:35])=[O:29].[CH:30]1([O:28][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([S:9][CH:6]3[CH2:8][CH2:7]3)=[CH:11][CH:12]=2)[C:17]2[NH:22][C:21](=[O:23])[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:19][CH:18]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1
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참가 물질

6

반응물 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 7298CyclopentanolHCID 67398402HCID 67398402, 화합물

생성물 2

HCID 6422Trifluoroacetic acid수율 0.1%HCID 58452349HCID 58452349, 화합물

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온도
100 °C

실험 절차

Methanesulfonic acid (250 μL) was added to a solution of 6-{[4-(cyclopropylsulfanyl)phenyl](hydroxy)methyl}-3-(trifluoromethyl)pyridin-2(1H)-one (40 mg) in cyclopentanol (500 μL), and the mixture was stirred at 100° C. for six hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by preparative HPLC (Waters Sunfire 19×150 mm 5 μm, rate: 20 mL/min, eluent: A=acetonitrile, B=0.1% trifluoroacetic acid solution, gradient: 10 to 90%) to give the title compound as a colorless amorphous (25 mg, 52%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customafter which the solvent was evaporated under reduced pressure
  4. customThe residue was purified by preparative HPLC (Waters Sunfire 19×150 mm 5 μm, rate

출처 및 근거

ORD 기록
ord-a623100dd4d94b999e66e38e1e60cfaa
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822503B2

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