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

HRID 1485949

反応式

HRID 1485949 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-96a31d542c644845889de818de7a31db
出典データセット
uspto-grants-2016_08
特許番号
US09422310B2

関連ノート

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