반응 #640550

반응 방정식

ethyl acetate

3-hydroxy-2-methylbenzoic acid

N-hydroxybenzotriazole

EDC

→

benzamide

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타1 hour
2. 2
   기타at is room temperature
3. 3
   workup.WAITAfter 15 hours at room temperature
4. 4
   세척washed with 5% citric acid, saturated sodium bicarbonate, brine
5. 5
   기타dried
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to afford 650 mg of crude material
9. 9
   기타This was chromatographed on silica gel using 0-25% ethyl acetate/methylene chloride as eluent

실험 절차

To a solution of 187 mg (1.23 mmol) of 3-hydroxy-2-methylbenzoic acid and 217 mg (1.61 mmol) of N-hydroxybenzotriazole in 6 mL of anhydrous N,N-dimethylformamide at 0° C., was added 236 mg (1.23 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at is room temperature, 450 mg (1.07 mmol) of 2R-hydroxy-3-[[(1,3-benzodioxol-5-yl)sulfonyl](2-methylpropyl)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 650 mg of crude material. This was chromatographed on silica gel using 0-25% ethyl acetate/methylene chloride as eluent to afford 390 mg of pure benzamide, N-[2R-hydroxy-3-[[(1,3-benzodioxol-5-yl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3-hydroxy-2-methyl, m/e=561(M+Li).

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