Réaction #640543

Équation de réaction

ethyl acetate

orthotoluoyl chloride

triethylamine

→

benzamide

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 5% citric acid, saturated sodium bicarbonate, brine
2. 2
   Autredried
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   Autreto afford 420 mg of crude material
6. 6
   AutreThis was chromatographed on 40 g of silica gel using 50% ethyl acetate/hexane

Mode opératoire

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).

Source