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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(((S)-3-hydroxypyrrolidin-1-yl)sulfonyl)benzamide

HRID 1427882
ノート
印刷プレビュー

反応式

HRID 1427882 の反応式
[C:1]12([CH2:11][O:12][C:13]3[C:39]([Cl:40])=[CH:38][C:16]([C:17]([NH:19][S:20]([N:23]4[CH2:27][CH2:26][C@H:25]([O:28]CC5C=CC(OC)=CC=5)[CH2:24]4)(=[O:22])=[O:21])=[O:18])=[C:15]([F:41])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O>[C:1]12([CH2:11][O:12][C:13]3[C:39]([Cl:40])=[CH:38][C:16]([C:17]([NH:19][S:20]([N:23]4[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24]4)(=[O:22])=[O:21])=[O:18])=[C:15]([F:41])[CH:14]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 867029064-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(((S)-3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamide

生成物 1

HCID 867029074-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(((S)-3-hydroxypyrrolidin-1-yl)sulfonyl)benzamide収率 58.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 6344
Dichloromethane
溶媒

実験手順

A mixture of 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N—(((S)-3-((4-methoxybenzyl)oxy)pyrrolidin-1-yl)sulfonyl)benzamide (0.17 g, 0.28 mmol) in dichloromethane (18 mL) and water (2 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.08 g, 0.36 mmol) at ambient temperature and stirred for 16 h. Water (20 mL) was added and the mixture extracted with ethyl acetate (80 mL×2), the combined organics were washed with brine; dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was filtered through a short silicon gel column, eluted with 5%-60% gradient ethyl acetate in hexanes to give the title compound as colorless solid (0.08 g, 55%): 1H NMR (300 MHz, DMSO-d6) δ 11.73 (s, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.21 (d, J=12.4 Hz, 1H), 5.07 (brs, 1H), 4.32-4.27 (m, 1H), 3.71 (s, 2H), 3.56-3.48 (m, 3H), 3.23-3.19 (m, 1H), 1.99 (s, 3H), 1.93-1.63 (m, 14H); MS (ES+) m/z 487.2, 489.1 (M+1); MS (ES−) m/z 485.3, 487.3 (M−1).

後処理

  1. extractionthe mixture extracted with ethyl acetate (80 mL×2)
  2. washthe combined organics were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationThe residue was filtered through a short silicon gel column
  6. washeluted with 5%-60% gradient ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-32e1ac2f9d68474d83db6274402e19ad
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933236B2

反応ノート

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