Hydrochloric Acid → [2'-(1-Ethyl-3-methyl-ureidomethyl)-5,4'-bis-trifluoromethyl-biphenyl-3-yl]-acetic acid

HRID 1810313Notes

Reaction equation

HRID 1810313 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[CH2:25][N:26]([CH2:31][CH3:32])[C:27]([NH:29][CH3:30])=[O:28])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.[Li+].[OH-].Cl>O1CCOCC1>[CH2:31]([N:26]([CH2:25][C:16]1[CH:17]=[C:18]([C:21]([F:23])([F:24])[F:22])[CH:19]=[CH:20][C:15]=1[C:7]1[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[CH:6]=1)[C:27]([NH:29][CH3:30])=[O:28])[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86651105[2'-(1-Ethyl-3-methyl-ureidomethyl)-5,4'-bis-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Product 1

HCID 54673043[2'-(1-Ethyl-3-methyl-ureidomethyl)-5,4'-bis-trifluoromethyl-biphenyl-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To [2′-(1-ethyl-3-methyl-ureidomethyl)-5,4′-bis-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester (0.18 mmol) was added 1:1 1N aqueous LiOH:1,4-dioxane (2 mL), and the reaction was stirred at room temperature for 30 minutes. 10% Aqueous HCl was added to acidify the solution to pH 3, and the mixture was extracted with EtOAc. The crude material was purified by silica gel chromatography to give the title compound. M+H is 463.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-516611baa3324354bd05dd4f9fce7864
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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