HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-[4-({3-[[(4-Phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl 3-[4-({3-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate | HCID 23143254 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-[4-({3-[[(4-Phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoic acid | HCID 23143257 | 75% |
Reaction Steps
To a mixture of methyl 3-[4-({3-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate (360 mg, 0.72 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 (262 mg, yield 75%) as colorless prism crystals (recrystallized from acetone-heptane).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07585880B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-2bae3ae2c21847fdbc14fd37fd841100 |
| Source note | uspto-grants-2009_09 |