1,2-Dichloroethane → Benzamide
Reaction equation
O[C:2]1[C:3](C)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].O[N:13]1C2C=CC=CC=2N=N1.C(Cl)CCl.C(OCC)(=O)C>CN(C)C=O>[C:5]([NH2:13])(=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1Participants
6
O[C:2]1[C:3](C)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].O[N:13]1C2C=CC=CC=2N=N1.C(Cl)CCl.C(OCC)(=O)C>CN(C)C=O>[C:5]([NH2:13])(=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1To a solution of 134 mg (0.88 mmol) of 3-hydroxy-2-methylbenzoic acid and 155 mg (1.15 mmol) of N-hydroxybenzotriazole in 5 mL of anhydrous N,N-dimethylformamide at 0° C., was added 167 mg (0.88 mmol) of EDC. After 20 minutes of activation at 0° C. and 1 hour at room temperature, 300 mg (1.0 mmol) of 2R-hydroxy-3-[(2-methylpropyl)(3-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 330 mg of crude material. This was chromatographed on silica gel using 30–70% ethyl acetate/methylene chloride as eluent to afford 230 mg of pure benzamide, N-[2R-hydroxy-3-[[(3-aminophenyl)sulfonyl](2-methylpropyl) amino]-1S-(phenylmethyl)propyl]-3-hydroxy-2-methyl.
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