Hydrochloric Acid → HCID 58565108, compound

HRID 554598Notes

Reaction equation

HRID 554598 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][N:13]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH:6]=1)C.[Li+].[OH-].O.Cl>CO.C1COCC1>[CH2:19]([N:13]([CH2:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[Br:11])[C:4]([OH:26])=[O:3])[C:14]([CH:16]1[CH2:17][CH2:18]1)=[O:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium Hydroxide2×HCID 58565224HCID 58565224, compound

Product 1

HCID 58565108HCID 58565108, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-bromo-benzoic acid ethyl ester (2.03 g, 4.9 mmol) was treated with 1N aqueous LiOH (10 mL) in MeOH (60 mL) and THF (10 mL). After stirring for 1 hour at room temperature, additional 1N aqueous LiOH (10 mL) was added, and the reaction was stirred for another 2 hours. The mixture was poured into H2O (200 mL) and neutralized with 1N aqueous HCl (50 mL). The solution was extracted three times with EtOAc to give 3-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-bromo-benzoic acid.

Workup

  1. stirringthe reaction was stirred for another 2 hours
  2. extractionThe solution was extracted three times with EtOAc

Sources & evidence

ORD record
ord-9085bab592524d96b070c1a0ee7f0c46
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

Loading…