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

HRID 448881

반응식

HRID 448881 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-495756f7fe1447b0b302c2f69182def8
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481738B2

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