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Acetic Acid → HCID 66909235、化合物

HRID 1969444
ノート
印刷プレビュー

反応式

HRID 1969444 の反応式
C(O)(=O)C.COC1CCC(OC)O1.FC(F)(F)C(O)=O.[F:21][C:22]([F:54])([F:53])[O:23][C:24]1[CH:25]=[C:26]([CH:30]2[N:34]([C:35]3[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=3)[C:33](=[O:43])[C:32](NC3C=CC(C#N)=CC=3)=[CH:31]2)[CH:27]=[CH:28][CH:29]=1.O=C1C(=O)[CH2:59][CH:58]([C:62]2[CH:67]=[CH:66][CH:65]=[C:64](OC(F)(F)F)[CH:63]=2)[N:57]1C1C=CC(C#N)=CC=1.C[C@@H](N)C1C=CC=CC=1>C1(C)C=CC=CC=1.C1COCC1.O>[O:43]=[C:33]1[C:32]([NH:57][C@@H:58]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH3:59])=[CH:31][C@@H:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([O:23][C:22]([F:21])([F:54])[F:53])[CH:25]=2)[N:34]1[C:35]1[CH:36]=[CH:37][C:38]([C:39]#[N:40])=[CH:41][CH:42]=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

10

反応物 6

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 6431891-Phenethylamine, (+)-HCID 66909199HCID 66909199、化合物HCID 66909220HCID 66909220、化合物

生成物 1

HCID 66909235
HCID 66909235、化合物
収率 26%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

Add acetic acid (6.32 mL, 110 mmol), 2,5-dimethoxytetrahydrofuran (10.7 mL, 82.8 mmol), water (25 mL), and trifluoroacetic acid (4.2 mL, 55.2 mmol) sequentially to a mixture of (±)-4-[5-(3-trifluoromethoxy-phenyl)-2-oxo-3-(4-cyano-phenylamino)-2,5-dihydro-pyrrol-1-yl]-benzonitrile (12.7 g, 27.6 mmol) and THF (83 mL). Heat the reaction mixture to 40° C. for 18 hours. Observe significant formation of (±)-4-[2,3-dioxo-5-(3-trifluoromethoxy-phenyl)-pyrrolidin-1-yl]-benzonitrile (LC-MS ESI m/z: 361 (M+H)+, Tr=2.34 min., method 2). Cool the reaction mixture to room temperature and add toluene (150 mL) in a single portion. Wash the mixture with water and then with brine. Dry over sodium sulfate, filter and add (R)-(+)-α-methyl benzylamine (7.1 mL, 55.2 mmol). Stir the solution at 45° C. for 1.75 hours. Concentrate the reaction mixture and purify by silica gel chromatography (15% EtOAc-hexane) to yield 4-[(S)-2-oxo-3-((R)-1-phenyl-ethylamino)-5-(3-trifluoromethoxy-phenyl)-2,5-dihydro-pyrrol-1-yl]-benzonitrile (3.34 g, 26%) as a red oil, LC-MS ESI m/z: 464 (M+H)+, Tr=3.09 min., method 2 and 4-[(R)-2-oxo-3-((R)-1-phenyl-ethylamino)-5-(3-trifluoromethoxy-phenyl)-2,5-dihydro-pyrrol-1-yl]-benzonitrile (4.05 g, 32%) as a foam, LC-MS ESI m/z: 464 (M+H)+, Tr=3.04 min., method 2.

後処理

  1. temperatureCool the reaction mixture to room temperature
  2. washWash the mixture with water
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationConcentrate the reaction mixture
  6. custompurify by silica gel chromatography (15% EtOAc-hexane)

出典と根拠

ORDレコード
ord-3cf73513a272479984529878ac5c12cc
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426448B2

反応ノート

読み込み中…

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