Reacción #640543

Ecuación de reacción

ethyl acetate

orthotoluoyl chloride

triethylamine

→

benzamide

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 5% citric acid, saturated sodium bicarbonate, brine
2. 2
   Otrodried
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   Otroto afford 420 mg of crude material
6. 6
   OtroThis was chromatographed on 40 g of silica gel using 50% ethyl acetate/hexane

Procedimiento

To a solution of 391 mg (1 mmol) of 2R-hydroxy-3-[(2-methylpropyl)(4-aminophenyl)sulfonyl]amino-1S-(phenylmethyl)propylamine in 3 mL of anhydrous methylene chloride, was added 0.42 mL (3 mmol) of triethylamine, then at room temperature, 0.12 mL (0.9 mmol) of orthotoluoyl chloride was added. After 15 hours at room temp ethyl acetate was added, washed with 5% citric acid, saturated sodium bicarbonate, brine, dried, filtered and concentrated to afford 420 mg of crude material. This was chromatographed on 40 g of silica gel using 50% ethyl acetate/hexane to afford 368 mg of pure benzamide, N-[2R-hydroxy-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl) amino]-1S-(phenylmethyl)propyl]-2-methyl, m/e=516(M+Li).

Fuente