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

HRID 517220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517220
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0bbad4f48781458db7aba2759625a4eb
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115093B2

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