反応 #640545

反応方程式

ethyl acetate

3-hydroxy-2-methylbenzoic acid

N-hydroxybenzotriazole

EDC

→

benzamide

収率 183.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.WAITAfter 15 hours at room temperature
2. 2
   洗浄washed with 5% citric acid, saturated sodium bicarbonate, brine
3. 3
   その他dried
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他to afford 590 mg of crude material
7. 7
   その他This was chromatographed on silica gel using 50-80% ethyl acetate/methylene chloride as eluent

実験手順

To a solution of 175 mg (1.15 mmol) of 3-hydroxy-2-methylbenzoic acid and 203 mg (1.5 mmol) of N-hydroxybenzotriazole in 6 mL of anhydrous N,N-dimethylformamide at 0° C., was added 220 mg (1.15 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at room temperature, 392 mg (1.0 mmol) of 2R-hydroxy-3-[(2-methylpropyl)(4-aminophenyl)sulfonyl]amino-1S-(phenylmethyl)propylamine was added. After 15 hours at room temperature, ethyl acetate was added, washed with 5% citric acid, saturated sodium bicarbonate, brine, dried, filtered and concentrated to afford 590 mg of crude material. This was chromatographed on silica gel using 50-80% ethyl acetate/methylene chloride as eluent to afford 255 mg of pure benzamide, N-[2R-hydroxy-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3-hydroxy-2-methyl, m/e=526(M+H).

出典