Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 9848045 | HCID 9848045 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 9825123 | HCID 9825123 | 88.7% |
Reaction Steps
LiOH (3.75 g, 0.1566 mol) dissolved in a minimum amount of water was added to (S)-1-[2-(1-phenylethylamino)pyrimidin-4-yl]-2-(3-trifluoromethylphenyl)-1H-imidazole-4-carboxylic acid ethyl ester (4.2 g, 0.0087 mol) in 20 mL THF. 3 mL MeOH was added and the solution warmed to 60° C. for 45 min. After cooling to room temperature, the reaction was acidified with pH 4.5 citric acid solution (buffered with NaOH) and extracted with ethyl acetate (2×150 mL). The ethyl acetate was dried over anhydrous magnesium sulfate and concentrated to give 3.5 g of a solid. The solid was stirred vigorously for 30 minutes as a slurry in Et2O and filtered to give the title compound (2.5 g ) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06492516B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-8ab78990d9dc43a19aba02e59ccd7fe8 |
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| Source note | uspto-grants-2002_12 |
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