Monoethyl malonate → (R)N-[1-(4-Bromo-phenyl)-ethyl]-malonamic Acid Ethyl Ester

HRID 858576

반응식

HRID 858576 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12][C:13](O)=[O:14].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:18]([O:17][C:11](=[O:16])[CH2:12][C:13]([NH:10][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:9])=[O:14])[CH3:19]

참가 물질

5

반응물 3

HCID 70615Monoethyl malonateHCID 757711-HydroxybenzotriazoleHCID 853000(R)-4-bromo-alpha-methylbenzylamine

생성물 1

HCID 58762223(R)N-[1-(4-Bromo-phenyl)-ethyl]-malonamic Acid Ethyl Ester수율 71.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a magnetically stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.51 g, 2.55 mmol) in anhydrous CH2Cl2 under argon and cooled to 0° C., were added ethyl hydrogen malonate (0.4 g, 3.06 mmol) EDC.HCl (0.58 g, 3.06 mmol) and HOBt (0.41 g, 3.06 mmol). The resulting solution was stirred at 25° C. overnight. CH2Cl2 was evaporate and residue partitioned between EtOAC and 1 N HCl. The organic layer was washed with H2O, brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (40% EtOAc in hexanes) to provide the desired product (0.57 g, 71%) as a white solid.

후처리

  1. customCH2Cl2 was evaporate
  2. customresidue partitioned between EtOAC and 1 N HCl
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography (40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-b69fd6196b72414d81b4d2877f6e7555
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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