2-Methyltetrahydrofuran → tert-Butyl (4-Cyano-2-methylphenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate

HRID 517220ノート

反応式

HRID 517220 の反応式
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:19]S(C2C=CC=CC=2)(=O)=O)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:7]([CH3:29])[CH:6]=1)#[N:4].CC1CCCO1.[F:36][C:37]([F:53])([F:52])[C:38]1[CH:39]=[C:40]([NH:44][C:45]2[CH2:50][CH2:49][CH2:48][C:47](=[O:51])[CH:46]=2)[CH:41]=[CH:42][CH:43]=1>O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:19][C:46]2[C:47](=[O:51])[CH2:48][CH2:49][CH2:50][C:45]=2[NH:44][C:40]2[CH:41]=[CH:42][CH:43]=[C:38]([C:37]([F:36])([F:53])[F:52])[CH:39]=2)[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[C:7]([CH3:29])[CH:6]=1)#[N:4]

参加物

6

反応物 4

HCID 73012-MethyltetrahydrofuranHCID 24758Sodium hydrideHCID 27486303-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-oneHCID 86732338tert-Butyl (4-Cyano-2-methylphenyl)(phenylsulfonyl)methylcarbamate

生成物 1

HCID 86732339tert-Butyl (4-Cyano-2-methylphenyl)(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methylcarbamate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Sodium hydride (60% in mineral oil, 150 mg, 3.75 mmol) is added in portions to a mixture of tert-butyl (4-cyano-2-methylphenyl)(phenylsulfonyl)methylcarbamate (step 1, 1.88 g, 3.41 mmol) and 2-methyltetrahydrofuran (10 mL), and the mixture is stirred at room temperature for 30 min 3-(3-(Trifluoromethyl)phenylamino)cyclohex-2-enone (869 mg, 3.41 mmol) is added, and the mixture is stirred for 2 h. Water is added, and the mixture is extracted with dichloromethane. The phases are separated, and the organic layer is concentrated under reduced pressure. The residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 1.57 g; ESI mass spectrum [M+H]+=500; Retention time HPLC: 0.79 min (X012_S01).

後処理

  1. additionis added
  2. extractionthe mixture is extracted with dichloromethane
  3. customThe phases are separated
  4. concentrationthe organic layer is concentrated under reduced pressure
  5. customThe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  6. custom0.79 min (X012_S01)

出典と根拠

ORDレコード
ord-0bbad4f48781458db7aba2759625a4eb
出典データセット
uspto-grants-2015_08
特許番号
US09115093B2

反応ノート

読み込み中…