Hydrochloric Acid → 3-(4-{2-Oxo-3-[4-(3-o-tolyl-ureido)phenyl]-2H-pyridin-1-ylmethyl}phenyl)-propionic acid

HRID 2218131Notes

Reaction equation

HRID 2218131 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[O:28])=[CH:22][CH:21]=3)[C:15]2=[O:37])=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>O1CCCC1.O>[O:37]=[C:15]1[C:16]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])=[O:28])=[CH:22][CH:21]=2)=[CH:17][CH:18]=[CH:19][N:14]1[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:38])=[O:3])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 104589693-(4-{2-Oxo-3-[4-(3-o-tolyl-ureido)phenyl)2H-pyridin-1-ylmethyl}phenyl)propionic acid ethyl ester

Product 1

HCID 98480513-(4-{2-Oxo-3-[4-(3-o-tolyl-ureido)phenyl]-2H-pyridin-1-ylmethyl}phenyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-{2-Oxo-3-[4-(3-o-tolyl-ureido)phenyl)2H-pyridin-1-ylmethyl}phenyl)propionic acid ethyl ester (P9, 55 mg, 0.11 mmol) and lithium hydroxide (50 mg, 2.5 mmol) were stirred at 60° C. for 30 minutes in tetrahydrofuran (5 mL) and water (5 mL). The reaction mixture was acidified to pH 1 with 1 N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was dried (anhydrous magnesium sulfate) and evaporated to dryness to afford the title compound as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-2179d957f873487f90b9370ccc5cc512
Source dataset
uspto-grants-2008_08
Patent number
US07410984B2

Reaction notes

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