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Hexane → 4-(8-Oxo-5-(4-(4-oxobutyl)phenyl)-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-2-(trifluoromethyl)benzonitrile

HRID 1192879
ノート
印刷プレビュー

反応式

HRID 1192879 の反応式
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:20](=[S:21])[N:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=3)[C:18](=[O:34])[C:14]32[CH2:17][CH2:16][CH2:15]3)=[CH:9][CH:8]=1.CCCCCC>ClCCl.[H-].C([Al+]CC(C)C)C(C)C>[O:34]=[C:18]1[C:14]2([CH2:17][CH2:16][CH2:15]2)[N:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][CH:3]=[O:2])=[CH:12][CH:11]=2)[C:20](=[S:21])[N:19]1[C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=1
参加物反応条件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 8058HexaneHCID 866300064-{4-[7-(4-Cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}-butyric acid methyl ester

生成物 1

HCID 252681274-(8-Oxo-5-(4-(4-oxobutyl)phenyl)-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-2-(trifluoromethyl)benzonitrile

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21225700
Diisobutylaluminumhydride
溶媒

反応条件

温度
21 °C

実験手順

To a stirred solution of 4-{4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}-butyric acid methyl ester (67) [ND-4] (61 mg, 0.12 mmol) in dichloromethane (5 mL), 1M diisobutylaluminum hydride (DIBAL) solution in hexane (0.16 mL, 0.16 mmol) was added at −78° C. After 30 min, the reaction mixture was quenched with saturated Rochelle's salt solution. The resulting mixture was stirred at 21° C. until both phases were clearly separated and the organic layer was clear. After extraction, the separated organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The crude mixture of (66) and (68) was purified by flash column chromatography (hexane:ethyl acetate,

後処理

  1. customthe reaction mixture was quenched with saturated Rochelle's salt solution
  2. customwere clearly separated
  3. extractionAfter extraction
  4. dry with materialthe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe crude mixture of (66) and (68)
  8. customwas purified by flash column chromatography (hexane

出典と根拠

ORDレコード
ord-df61238aeb014f8fbb2c29a558018860
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680291B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート