HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → {2-[5-{[6-(Methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | ethyl{2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate | HCID 58081032 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | {2-[5-{[6-(Methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid | HCID 66726112 | 71.1% |
Reaction Steps
A mixture of ethyl{2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (1.04 g), 1M aqueous sodium hydroxide solution (6 mL), tetrahydrofuran (10 mL), and ethanol (10 mL) was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was neutralized with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (700 mg, yield 71%) as a white amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08557805B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-53577185ad5f48faa8926a0481bfa8cd |
| Source note | uspto-grants-2013_10 |