HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → (R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | (R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester | HCID 58497400 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (R)-3-[3-(4,6-Dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid | HCID 58497409 | 88% |
Reaction Steps
To a solution of (R)-3-[3-(4,6-dimethyl-benzo[d]isothiazol-3-ylmethyl)-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester (10 mg, 0.021 mmol) in 1,4-dioxane (5 mL) and water (1 mL) was added lithium hydroxide (LiOH) (0.9 mg, 0.042 mmol) at room temperature. The solution was stirred at the same temperature for 4 hours. The solution was concentrated and water was added to the residue. The solution was acidified by 12N HCl in an ice-bath. The solution was concentrated and the residue was purified by preparative TLC with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (8.3 mg, 88%): LCMS, M++1, m/z: 459.13 as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09062056B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-160a8cdcf5d34b6bae25bc091935e539 |
| Source note | uspto-grants-2015_06 |