HuagongsheHuagongshe Chemistry Print Report · For research reference only
Succinic anhydride → HCID 131728226, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Succinic anhydride | HCID 7922 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione | HCID 131728225 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 131728226 | HCID 131728226 | 89.6% |
Reaction Steps
Referring to scheme 19, Compound 77 (2 g, 3 mmol) was mixed with succinic anhydride (0.600 g, 6 mmol) and DMAP (0.366 g, 3 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (5 mL), triethylamine (0.913 g, 1.25 mL, 9 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 4 h. It was then diluted with dichloromethane (50 mL) and washed with ice cold aqueous citric acid (5% wt., 50 mL) and water (2×50 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by column chromatography using 6% MeOH/DCM to afford compound 79 as white solid (2.05 g, 89% yield; Rf=0.4 in 10% MeOH/CHCl3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394540B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-53ff139a656b4f289118538ebd4b31ea |
| Source note | uspto-grants-2016_07 |