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 515320ノート

反応式

HRID 515320 の反応式
[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]

参加物

5

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 86670956HCID 86670956、化合物

生成物 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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

(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]+

後処理

  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)

出典と根拠

ORDレコード
ord-3b4ad3ff30a142db84920115a4639a3d
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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