Hydrochloric Acid → 3-[4-({4-[[(4-Phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoic acid

HRID 732190Notes

Reaction equation

HRID 732190 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][N:13]([CH2:34][CH2:35][CH3:36])[C:14]3[CH:33]=[CH:32][C:17]([CH2:18][O:19][C:20]4[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[OH-].[Na+].Cl>O.O1CCCC1>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][N:13]([CH2:34][CH2:35][CH3:36])[C:14]3[CH:33]=[CH:32][C:17]([CH2:18][O:19][C:20]4[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23143239Methyl 3-[4-({4-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate

Product 1

HCID 231433083-[4-({4-[[(4-Phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoic acidYield 32.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-[4-({4-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate (240 mg, 0.48 mmol), ethanol (5 mL) and tetrahydrofuran (5 mL) was added 2N aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-4:1 in volume ratio) to give the title compound (75 mg, yield 32%) as colorless prism crystals (recrystallized from acetone-heptane).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-4:1 in volume ratio)

Sources & evidence

ORD record
ord-2f6b5c8e72f045e192ac59750c6db139
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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