Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 10233544 | HCID 10233544 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 9917719 | HCID 9917719 | 94% |
Reaction Steps
A mixture of methyl 3-[4-[6-(4-adamantan-1-ylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]phenyl]-2-(4-fluorobenzyloxy)propionate (0.25 g), aqueous 2N sodium hydroxide solution (2 ml) and methanol (5 ml) was stirred at room temperature for 2 hours. To the reaction mixture was added tetrahydrofuran (5 ml) and the mixture was stirred for 4 hours. The reaction mixture was poured into water and neutralized with hydrochloric acid and sodium hydrogencarbonate and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The ethyl acetate was evaporated under reduced pressure. The residue crystallized in ethyl acetate and the crystals were isolated by filtration to afford the title compound (0.23 g, mp 148-149° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06596751B2 |
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| Source dataset | uspto-grants-2003_07 |
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| ORD ID | ord-f5d5703c80844e54bce4406217a4c410 |
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| Source note | uspto-grants-2003_07 |
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