Sodium hydride → 4-(N-(2-Cyclohexylethyl)-N-p-toluenesulfonylaminomethyl)-2-(2-methylphenyl)benzoic acid, Methyl Ester

HRID 383136Notes

Reaction equation

HRID 383136 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[H-].[Na+].[CH3:22][O:23][C:24](=[O:40])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Br)=[CH:27][C:26]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39]>CN(C=O)C>[CH:2]1([CH2:7][CH2:8][N:9]([CH2:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([O:23][CH3:22])=[O:40])=[C:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])[CH:27]=2)[S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:1]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18360914N-2-cyclohexylethyl-p-toluenesulfonamideHCID 234362594-Bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester

Product 1

HCID 206998624-(N-(2-Cyclohexylethyl)-N-p-toluenesulfonylaminomethyl)-2-(2-methylphenyl)benzoic acid, Methyl EsterYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-2-cyclohexylethyl-p-toluenesulfonamide (300 mg) in DMF (5 mL) was added NaH (56 mg of a 60% dispersion in mineral oil). After gas evolution subsided, 4-bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester (example 1178D, 266 mg) was added. After stirring at ambient temperature for 1.5 h, the reaction was quenched by addition of water (10 mL), and diluted with 50% EtOAc/hexane (50 mL). The organic solution was washed with water (10 mL), brine (2×10 mL), dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography eluting with 10% EtOAc/hexane to give the title compound as a colorless oil (250 mg, 70%).

Workup

  1. customthe reaction was quenched by addition of water (10 mL)
  2. additiondiluted with 50% EtOAc/hexane (50 mL)
  3. washThe organic solution was washed with water (10 mL), brine (2×10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-6c64c481df8740ba8dac742062e29fcf
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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