Diisopropylethylamine → 4-[2-(3-Bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester

HRID 1485948

反応式

HRID 1485948 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[CH3:12][O:13][C:14](=[O:25])[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:25])[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Br:1])[CH:3]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 237256Methyl 4-(2-aminophenyl)butanoateHCID 202297303-Bromo-4-chlorobenzoyl chloride

生成物 1

HCID 686021474-[2-(3-Bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester収率 101.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 3-bromo-4-chloro-benzoyl chloride (1.09 g, 4.3 mmol) in DCM (30 mL) cooled with an ice bath, was added 4-(2-amino-phenyl)-butyric acid methyl ester (0.85 g, 4.4 mmol), followed by addition of diisopropylethylamine (1 mL, 5.6 mmol) slowly. Upon the completion of the addition, ice bath was removed and the mixture was stirred at room temperature for 12 hrs. The mixture was further diluted with DCM, washed with saturated NaHCO3, 1N HCl, brine and dried over Na2SO4 and concentrated to yield 4-[2-(3-bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester (1.8 g). MS [M+H]+: 411.7; tR=2.45 min. (method 1)

後処理

  1. additionUpon the completion of the addition, ice bath
  2. customwas removed
  3. additionThe mixture was further diluted with DCM
  4. washwashed with saturated NaHCO3, 1N HCl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-68351de091e246ce87bde63f435e25f8
出典データセット
uspto-grants-2016_08
特許番号
US09422310B2

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