Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Reactant | HCID 59331231 | HCID 59331231 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59331293 | HCID 59331293 | 77.9% |
Reaction Steps
A mixture of ethyl 3-[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]propanoate (0.46 g), 1M aqueous sodium hydroxide solution (1.7 mL), methanol (3 mL) and tetrahydrofuran (6 mL) was stirred at room temperature overnight. To the reaction mixture was added 1M hydrochloric acid (1.7 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a yellow amorphous solid. To a mixture of the obtained amorphous solid, 1M aqueous sodium hydroxide solution (1.0 mL), methanol (1 mL) and water (10 mL) was added a solution of calcium chloride (94 mg) in water (2 ml). The precipitated solid was collected by filtration, washed with water, and dried to give the title compound (0.34 g) as yellow crystals. melting point>194° C. (decomposition). MS: 515 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318746B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-d2ef7274a8e9470ebc44ae6959ac3dc8 |
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| Source note | uspto-grants-2012_11 |
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