m-Chloroperbenzoic acid → 1-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-ylsulfinyl)phenyl)-3-((S)-tetrahydrofuran-3-yl)urea

HRID 515320노트

반응식

HRID 515320 반응식
[F:1][C:2]([F:39])([F:38])[C:3]([C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([S:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C@H:31]4[CH2:35][CH2:34][O:33][CH2:32]4)=[O:29])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].ClC1C=C(C=CC=1)C(OO)=[O:45]>ClCCl.CO>[F:5][C:4]([F:7])([F:6])[C:3]([C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([S:20]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C@H:31]4[CH2:35][CH2:34][O:33][CH2:32]4)=[O:29])=[CH:23][CH:22]=3)=[O:45])[CH2:18][CH2:19]2)=[CH:11][CH:10]=1)([OH:8])[C:2]([F:38])([F:1])[F:39]

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 86670956HCID 86670956, 화합물

생성물 1

HCID 866709571-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-ylsulfinyl)phenyl)-3-((S)-tetrahydrofuran-3-yl)urea

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

(S)-1-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-ylthio)phenyl)-3-(tetrahydrofuran-3-yl)urea (0.246 mmol, 142 mg) was dissolved in dichloromethane (5 mL) and the solution cooled to 0° C. 3-Chlorobenzoperoxoic acid (0.246 mmol, 42.4 mg) was added and the reaction mixture stirred for 2 hours. The reaction mixture was diluted with methanol and dichloromethane. The reaction mixture was washed with water and the organic layer separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with a dichloromethane/methanol/ammonia gradient) to afford the title compound. MS m/z 594.5 [M+H]+

후처리

  1. washThe reaction mixture was washed with water
  2. customthe organic layer separated
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica column chromatography (
  6. washeluting with a dichloromethane/methanol/ammonia gradient)

출처 및 근거

ORD 기록
ord-3b4ad3ff30a142db84920115a4639a3d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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