반응 #89765
ord-06c6610729224d2195a88b09188a18f4
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시약
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후처리
- 1온도cooled to rt
- 2기타to 0° C
- 3여과Filtration
- 4기타afforded a clear solution
- 5기타The reaction was quenched with saturated aqueous NH4Cl
- 6추출extracted with EtOAc (2×)
- 7세척The combined organic layers were washed with brine
- 8건조dried over sodium sulfate
- 9여과filtered
- 10농축concentrated in vacuo
- 11기타The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O
- 12기타to give the product
실험 절차
To a stirred suspension of hydroxylamine hydrochloride (1.56573 g, 0.0223062 mol) in anhydrous methanol (6.0 mL) at rt was added 4.37 M of sodium methoxide in methanol (7.64 mL). The reaction mixture was heated at 55° C. for 5 min, cooled to rt, then to 0° C. Filtration afforded a clear solution assumed to be ca. 1.50 M in methanol. To a stirred solution of methyl(3R,4S)-1-[(E)-(cyanoimino)(piperidin-1-yl)methyl]-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate (53.30 mg, 0.0001054 mol) in anhydrous methanol (1.110 mL, 0.02740 mol) at rt was added the above 1.50 M of hydroxylamine in methanol (1.40 mL). The reaction mixture was stirred at rt for 2 h. LCMS showed the reaction was done. The reaction was quenched with saturated aqueous NH4Cl, extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O to give the product. MS (ESI): (M+H)+=507.