Hydrochloric Acid → HCID 66604173, compound

HRID 2197354Notes

Reaction equation

HRID 2197354 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:37][CH3:38])[C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[O:27])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[Li+].[OH-].Cl>C1COCC1.CO>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][NH:28][C:26](=[O:27])[N:25]([CH2:24][C:15]2[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:14]=2[C:8]2[C:9]([O:12][CH3:13])=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:39])=[O:3])[CH:7]=2)[CH2:37][CH3:38])=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66604157HCID 66604157, compound

Product 1

HCID 66604173HCID 66604173, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To {2′-[3-(4-chloro-benzyl)-1-ethyl-ureidomethyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester (0.196 g, 0.35 mmol) in THF (2 mL) and MeOH (2 mL) was added 1N aqueous LiOH (2 mL), and the reaction was stirred at room temperature for 2 hours. The mixture was acidified with 1N aqueous HCl and extracted three times with EtOAc, and the combined organic layers were dried and concentrated. The residue was purified by preparative HPLC to give the title compound.

Workup

  1. extractionextracted three times with EtOAc
  2. customthe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-164bf23a2bd5413dbc9c3a420524eacc
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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