1,2-Dichloroethane → Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate

HRID 1352809노트

반응식

HRID 1352809 반응식
[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

참가 물질

5

반응물 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 102312Benzyloxyamine hydrochlorideHCID 225750493,5-Bis(ethoxycarbonyl)benzoate

생성물 1

HCID 12017544Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate수율 58.9%

실험 절차

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).

후처리

  1. customThe solvent was removed by evaporator
  2. dissolutionthe residue was dissolved in EtOAc (150 mL)
  3. washThe organic solution was washed with 1 N HCL (150 mL)
  4. washwashed with saturated aqueous NaHCO3 (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give white solid
  8. customThis material was recrystallized from EtOAc

출처 및 근거

ORD 기록
ord-7db6242a6e1e4d0f8bc2279e0de434c6
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220780B2

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