Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 67296455 | HCID 67296455 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67296202 | HCID 67296202 | 77% |
Reaction Steps
2-Methyl-2-{4-[(1R,3S)-3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}propanoic acid ethyl ester (130 mg, 0.29 mmol) was dissolved in ethanol (2 mL) and tetrahydrofuran (2 mL), followed by addition of 2N aqueous potassium hydroxide solution, and the mixture was stirred overnight at room temperature. 1N hydrochloric acid was added dropwise to the reaction mixture to make the reaction solution acidic, and the solvent was distilled off under reduced pressure. The aqueous phase was extracted with ethyl acetate, 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 ethyl acetate (3 mL), followed by addition of an ethyl acetate solution of 1N hydrochloric acid (1 mL), and 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 (102 mg, 77%).
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-e56ebb62c36544beb5b0b14c62aa401c |
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| Source note | uspto-grants-2015_09 |
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