Hydrochloric Acid → 4-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid

HRID 1485952Notes

Reaction equation

HRID 1485952 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Br:23])[CH:17]=1)[CH3:14].Cl>C1COCC1.[Li+].[OH-]>[Br:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[Cl:22])[C:15]([N:13]([CH3:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2])=[O:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 686026204-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester

Product 1

HCID 686025894-{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acidYield 103%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid methyl ester (1.11 g, 2.6 mmol, Step 13D) in THF (8 mL), 2N LiOH (6.5 mL) was added and the mixture was stirred for 2 hours at rt. 1N HCl was added to the reaction mixture to yield a pH ˜2 followed by extraction with EtOAc (2×). The combined organic layers were washed with water and brine, dried (Na2SO4) and concentrated in vacuo to afford 1.1 g of 4-{2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenyl}-butyric acid as a white solid. MS [M+H]+: 411.7; tR=2.57 min, (method 1)

Workup

  1. customto yield a pH ˜2
  2. extractionfollowed by extraction with EtOAc (2×)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c850a77f3b784da2864bef4b229ad1f7
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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