Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 53357737 | HCID 53357737 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 53357998 | HCID 53357998 | 94.1% |
Reaction Steps
A solution of chiral methyl 5-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)benzofuran-2-carboxylate (80.7 mg, 0.126 mmol) in THF (6 ml) was reacted with LITHIUM HYDROXIDE MONOHYDRATE (222.3 mg, 0.531 mmol) in water (3 ml) and stirred at rt for 3 hrs. The reaction treated with 1 N HCl (pH 3-4) and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried with sodium sulfate, filtered and lyophilized to give chiral-5-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)benzofuran-2-carboxylic acid (74.3 mg, 94.1%) as a white solid. MS (ES+) m/z Calcd: [(M+H)+]: 626.13. found: 626.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08354444B2 |
|---|
| Source dataset | uspto-grants-2013_01 |
|---|
| ORD ID | ord-13a9e70133b847e0b07314e734517e90 |
|---|
| Source note | uspto-grants-2013_01 |
|---|