Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate | HCID 67548625 | — |
| Solvent | MeOH tetrahydrofuran | HCID 21899815 | — |
| Product | HCID 60135938 | HCID 60135938 | 54.2% |
Reaction Steps
A 2 N aqueous lithium hydroxide solution (1.30 mL, 2.59 mmol) was added to a mixed solution of ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (227d) (114 mg, 0.26 mmol) in methanol/THF (3 mL/0.5 mL), and the mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (4.5 mL) was added to the aqueous layer, followed by extraction with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting solid was suspended and washed in diethyl ether to obtain 58 mg of the title compound as a white solid (54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08536197B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-4daf5cf56b1941d5bb3a7b8698542579 |
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| Source note | uspto-grants-2013_09 |
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