2-Methyltetrahydrofuran → tert-Butyl(4-Cyanophenyl)(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)methylcarbamate

HRID 927196Notes

Reaction equation

HRID 927196 reaction equation
[H-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH2:16][CH2:15][C:14](=[O:17])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1.CC1CCCO1.[C:26]([O:30][C:31](=[O:51])[N:32]([C:43]1[CH:48]=[CH:47][C:46]([C:49]#[N:50])=[CH:45][CH:44]=1)[CH2:33]S(C1C=CC=CC=1)(=O)=O)([CH3:29])([CH3:28])[CH3:27]>O>[C:26]([O:30][C:31](=[O:51])[N:32]([C:43]1[CH:44]=[CH:45][C:46]([C:49]#[N:50])=[CH:47][CH:48]=1)[CH2:33][C:13]1[C:14](=[O:17])[CH2:15][CH2:16][C:12]=1[NH:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:18])([F:19])[F:3])[CH:6]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 24758Sodium hydrideHCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-oneHCID 129539717Tert-butyl(4-cyanophenyl)(phenylsulfonyl)methylcarbamate

Product 1

HCID 131735047tert-Butyl(4-Cyanophenyl)(5-oxo-2-(3-(trifluoromethyl)phenylamino)cyclopent-1-enyl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in mineral oil, 1.06 g, 26.5 mmol) is added at room temperature in portions to a mixture of 3-(3-(trifluoromethyl)phenylamino)cyclopent-2-enone (4.31 g, 17.9 mmol) and 2-methyltetrahydrofuran. After 20 min tert-butyl(4-cyanophenyl)(phenyl-sulfonyl)methylcarbamate (10.0 g, 24.2 mmol based on 90% purity) is added, and the mixture is stirred at room temperature for 1 h. Water is added and the phases are separated. The organic layer is washed with water and concentrated under reduced pressure, and the residue is recrystallized from tert-butyl methyl ether. Yield: 6.92 g. ESI mass spectrum: [M+H]+=472; Retention time HPLC: 0.76 min (X012_S01).

Workup

  1. customthe phases are separated
  2. washThe organic layer is washed with water
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is recrystallized from tert-butyl methyl ether
  5. custom0.76 min (X012_S01)

Sources & evidence

ORD record
ord-63c9f730e1a74a3a9c8755308b2e4f35
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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