2-Methyltetrahydrofuran → {(4-Cyano-2-methylsulfanyl-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester

HRID 59643Notes

Reaction equation

HRID 59643 reaction equation
[H-].[Na+].[F:3][C:4]([F:20])([F:19])[C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1.CC1CCCO1.[C:27]([O:31][C:32](=[O:54])[NH:33][CH:34](S(C1C=CC=CC=1)(=O)=O)[C:35]1[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][C:36]=1[S:43][CH3:44])([CH3:30])([CH3:29])[CH3:28]>O>[C:27]([O:31][C:32](=[O:54])[NH:33][CH:34]([C:35]1[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][C:36]=1[S:43][CH3:44])[C:13]1[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:12]=1[NH:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:19])([F:20])[F:3])[CH:6]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 73012-Methyltetrahydrofuran2×HCID 24758Sodium hydrideHCID 27486303-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one2×HCID 118692905[Benzenesulfonyl-(4-cyano-2-methylsulfanyl-phenyl)-methyl]-carbamic acid tert-butyl ester

Product 1

HCID 118692901{(4-Cyano-2-methylsulfanyl-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in mineral oil, 154 mg, 3.85 mmol) is added in portions to a mixture of 3-(3-trifluoromethyl-phenylamino)-cyclohex-2-enone (INTERMEDIATE 3; 960 mg, 3.76 mmol) and 2-methyltetrahydrofuran (8 mL). After 30 min [benzenesulfonyl-(4-cyano-2-methylsulfanyl-phenyl)-methyl]-carbamic acid tert-butyl ester (Step 1, 1.56 g, 3.73 mmol) is added and the mixture is stirred at room temperature for 50 min. Water and 2-methyltetrahydrofuran are added and the phases are separated. The organic phase is dried over Na2SO4 and concentrated under reduced pressure. Yield: 2.13 g. ESI mass spectrum: [M+H]+=532; Retention time HPLC: 1.22 min (Z018_S04).

Workup

  1. customthe phases are separated
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custom1.22 min (Z018_S04)

Sources & evidence

ORD record
ord-4fc9aab3527f4474ba16efc1a0378fb6
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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