HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → HCID 59401140, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3-Quinuclidinol, (-)- | HCID 91404 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | (2-Fluoro-phenylamino)-phenyl-acetic acid hydrochloride | HCID 67425879 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59401140 | HCID 59401140 | 16.3% |
Reaction Steps
A solution of DCC (534 mg, 0.71 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (217 mg, 1.42 mmol), (2-fluoro-phenylamino)-phenyl-acetic acid hydrochloride (I247) (200 mg, 0.71 mmol) and (R)-quinuclidin-3-ol (271 mg, 2.13 mmol) in THF (10 mL) is stirred at RT for 2 days. The solvent is evaporated and the residue is taken up with EtOAc, washed with sat NaHCO3, water and brine. The organic layer is collected, dried over Na2SO4, filtered and evaporated to dryness. The residue is purified by preparative HPLC. The organic solvent is evaporated and the acid aqueous phase is basified with Na2CO3 and extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and evaporated to afford the title compound as yellow oil (41 mg, 16% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08835682B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-6cbc504d915e4120ada07cb5a4a21d97 |
| Source note | uspto-grants-2014_09 |