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

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%).

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

ORD 기록

ord-6c64c481df8740ba8dac742062e29fcf

출처 데이터셋

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06310095B1