Water → 2-[ethyl-(4-fluorophenyl)sulfonyl-amino]N-[[1-oxido-2-[4-(trifluoromethyl)phenyl]pyridin-1-ium-4-yl]methyl]prop-2-enamide

HRID 1479881노트

반응식

HRID 1479881 반응식
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([N:14]([S:37]([C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38])[C:15](=[CH2:36])[C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH:21]=1)=[O:17])[CH3:13].O.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[CH2:12]([N:14]([S:37]([C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38])[C:15](=[CH2:36])[C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][N+:23]([O-:9])=[C:22]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)[CH:21]=1)=[O:17])[CH3:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 783246012-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamide

생성물 1

HCID 903900472-[ethyl-(4-fluorophenyl)sulfonyl-amino]N-[[1-oxido-2-[4-(trifluoromethyl)phenyl]pyridin-1-ium-4-yl]methyl]prop-2-enamide수율 29%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

3-Chloro perbenzoic acid (1.5 mol eq, 100 mg) was added to a solution of Example 1 (200 mg, 0.39 mmol) in CHCl3 (10 mL) and the mixture was stirred at r.t. for 24 hours. Then 10% water solution of K2CO3 was added to wash the organic phase that was then dried over Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (EtOAc 6/petroleum ether 4) to obtain a white solid (60 mg, 29% yield). 1HNMR (DMSO, 200 MHz) δ 1.09 (3H, t, J=7.2 Hz), 3.40 (2H, q, J=6.8 Hz), 4.40 (2H, d, J=6 Hz), 5.14 (1H, s), 6.10 (1H, s), 7.36 (1H, dd, J=4.8 Hz, J′=1.2 Hz), 7.46 (2H, t, J=8.8 Hz), 7.63 (1H, d, J=2.2 Hz), 7.83 (4H, m), 8.05 (2H, d, J=8 Hz), 8.34 (1H, d, J=6.8 Hz), 8.82 (1H, bt) [M+1] 524.6 (C24H21F4N3O4S requires 523.50).

후처리

  1. washto wash the organic phase that
  2. dry with materialwas then dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe resulting residue was purified by flash chromatography (EtOAc 6/petroleum ether 4)

출처 및 근거

ORD 기록
ord-5ecb31d833f74712828f6566776dbe93
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409864B2

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