HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → HCID 72550214, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Ammonium Bicarbonate | HCID 14013 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | HCID 60155116 | HCID 60155116 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 72550214 | HCID 72550214 | 59.5% |
Reaction Steps
To a solution of 4-(((1R,2R)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoic acid (100 mg, 0.26 mmol) in DMSO (5 mL) was added Boc anhydride (69 mg, 0.31 mmol) followed by pyridine (24 mg, 0.26 mmol) and stirred at room temperature for 5 min. Ammonium bicarbonate (62 mg, 0.78 mmol) was added and stirred for additional 1 h. Reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine (25 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by CombiFlash using 20% ethyl acetate in chloroform as an eluent to yield 59 mg (59%) of the title compound as an off white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260376B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-158bfbe895e54617a069ac760a1b63aa |
| Source note | uspto-grants-2016_02 |