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

HRID 1485948

Reaction equation

HRID 1485948 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-68351de091e246ce87bde63f435e25f8
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Linked notes

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