1,2-Dichloroethane → Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate
反応式
[C:1]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=[C:5]([C:7]([O-:9])=O)[CH:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=1.Cl.[CH2:21]([O:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN1CCOCC1.C(Cl)CCl>>[C:22]1([CH2:21][O:28][NH:29][C:7]([C:5]2[CH:4]=[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=[C:1]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=2)=[O:9])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1参加物
実験手順
To a solution of diethyl 1,3,5-benzenetricarboxylate (3.192 g, 20 mol) and O-benzylhydroxyamine hydrochloride (4.789 g, 19 mmol) in 40 mL were added N-methylmorpholine (2.2 mL, 20 mmol) and EDC (3.834 g, 20 mmol) at 0° C., and the mixture was stirred at room temperature for 20 hours. The solvent was removed by evaporator and the residue was dissolved in EtOAc (150 mL). The organic solution was washed with 1 N HCL (150 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over Na2SO4, and concentrated to give white solid. This material was recrystallized from EtOAc to give 4.154 g of white powder: 1H NMR (CDCl3) δ 1.41 (t, 6H), 4.40 (q, 4H), 5.05 (s, 2H), 7.3-7.5 (m, 5H), 8.52 (s, 2H), 8.76 (s, 1H), 9.1 (br, 1H). TLC: Rf 0.62 (EtOAc/Hexanes 1/1).
後処理
- customThe solvent was removed by evaporator
- dissolutionthe residue was dissolved in EtOAc (150 mL)
- washThe organic solution was washed with 1 N HCL (150 mL)
- washwashed with saturated aqueous NaHCO3 (50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customto give white solid
- customThis material was recrystallized from EtOAc
出典と根拠
- ORDレコード
- ord-7db6242a6e1e4d0f8bc2279e0de434c6
- 出典データセット
- uspto-grants-2007_05
- 特許番号
- US07220780B2
反応ノート
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