Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 59617257 | HCID 59617257 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67296283 | HCID 67296283 | 87% |
Reaction Steps
{4-[(1R,3S)-3-{[(1R)-1-(Naphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}acetic acid ethyl ester (720 mg, 1.7 mmol) was dissolved in ethanol (5 mL), followed by addition of 1N aqueous sodium hydroxide solution (5 mL), and the mixture was stirred for 1 hour at room temperature. 1N hydrochloric acid was added dropwise to the reaction mixture to make the reaction solution acidic, and then the solvent was distilled off under reduced pressure. The aqueous phase was extracted with methylene chloride, the extracted solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained was dissolved in methylene chloride (6 mL), followed by addition of an ethyl acetate solution of 1N hydrochloric acid (2 mL), and then the solvent was distilled off under reduced pressure. Ethyl acetate and hexane were added to the residue, followed by treatment with ultrasonic waves, and then the solid matter generated was collected by filtration to give the title compound (237 mg, 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133140B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-c851123870024aefacf8db5422e3b892 |
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| Source note | uspto-grants-2015_09 |
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