반응 #640543

반응 방정식

ethyl acetate

orthotoluoyl chloride

triethylamine

→

benzamide

용매

methylene chloride

반응 조건

후처리

1. 1
   세척washed with 5% citric acid, saturated sodium bicarbonate, brine
2. 2
   기타dried
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to afford 420 mg of crude material
6. 6
   기타This was chromatographed on 40 g of silica gel using 50% ethyl acetate/hexane

실험 절차

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).

출처