Methyl iodide → 4-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester

HRID 661634

반응식

HRID 661634 반응식
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Br:22])[CH:16]=1.[H-].[Na+].I[CH3:28]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Br:22])[CH:16]=1)[CH3:28]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 686021474-[2-(3-Bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester

생성물 1

HCID 686026204-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester수율 92.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To 4-[2-(3-bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester (1.04 g, 2.54 mmol) in DMF (10 mL) at 0-5° C., was added NaH (152 mg, 3.81 mmol, 60% in mineral oil) in two portions. The mixture was stirred for 15 min at 0° C. and 15 min at rt. After addition of iodomethane (316 μl, 5.08 mmol), the mixture was stirred at room temperature for 12 hrs and was partitioned between ethyl acetate and citric acid. The separated organic layer was then washed with brine and dried over Na2SO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (4/1) up to hexane/ethyl acetate (3/2) yielded 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester (1.0 g). MS [M+H]+: 426.0; tR=2.46 min. (method 1)

후처리

  1. stirringthe mixture was stirred at room temperature for 12 hrs
  2. customwas partitioned between ethyl acetate and citric acid
  3. washThe separated organic layer was then washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and purification by silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (4/1) up to hexane/ethyl acetate (3/2)

출처 및 근거

ORD 기록
ord-169657d1668b44579ef10f2ae4566e2f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

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