Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 59830708 | HCID 59830708 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59830697 | HCID 59830697 | 105.4% |
Reaction Steps
A solution of lithium hydroxide (0.055 g, 1.29 mmol) in water (1 mL) was added dropwise to a stirred solution of methyl {(3S)-1-[6-(propylthio)-5-(tetrahydro-2H-pyran-4-ylcarbamoyl)pyridin-2-yl]piperidin-3-yl}acetate (188 mg, 0.43 mmol) in MeOH (3 mL) and THF (2 mL) at 18° C., over a period of 1 minute. The resulting solution was stirred at 18° C. for 20 hours. The reaction mixture was adjusted to pH 4.5 with 2M HCl and the reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford {(3S)-1-[6-(propylthio)-5-(tetrahydro-2H-pyran-4-ylcarbamoyl)pyridin-2-yl]piperidin-3-yl}acetic acid (191 mg, 100%), as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07964618B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-839ee4f3d3ae4ca599da08bedf46f01a |
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| Source note | uspto-grants-2011_06 |
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