Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 57709041 | HCID 57709041 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23691964 | HCID 23691964 | 57% |
Reaction Steps
Methanol (1.3 mL), tetrahydrofuran (1.3 mL) and a 1 M sodium hydroxide aqueous solution (0.129 mL, 0.129 mmol) were added to [4′-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-3-fluoro-2′-methyl-biphenyl-4-yl]-acetic acid methyl ester (Example 84-(1); 22.8 mg, 0.043 mmol), and the mixture was stirred at room temperature for 25 hours. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and then the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was crudely purified by preparative TLC (chloroform/methanol=10/1). The crude purified product was diluted with methanol. After addition of sodium methoxide, the mixture was dried under reduced pressure. The residue was purified by preparative TLC (developer obtained by saturating chloroform/methanol=10/1 with water). The purified product was diluted with methanol. After addition of sodium methoxide, the mixture was dried under reduced pressure to give the title compound (12.6 mg, 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07935688B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-cae3a927d6784ae681c34e03b2f2401b |
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| Source note | uspto-grants-2011_05 |
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