HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 10272714, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl bromoacetate | HCID 60984 | — |
| Reactant | HCID 21055258 | HCID 21055258 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10272714 | HCID 10272714 | 61.3% |
Reaction Steps
A slurry of 5-benzyl-1-hydroxy-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-10-carboxylic acid amide (Part F; 275 mg; 0.822 mmol) and Cs2CO3 (670 mg; 2.06 mmol) in 8 mL of DMF was treated with methyl bromoacetate (0.100 mL; 1.07 mmol). After stirring overnight at ambient temperature, the reaction mixture was poured into water and EtOAc (20 mL each). The layers were separated, and the organic phase was washed with water (3×20 mL), dried over Na2SO4 and concentrated in vacuo. Purification by radial chromatography (CHCl3) afforded 205 mg (0.504 mmol; 61%) of the title ester as a white foam. ES-MS: 407 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07109231B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-26a3baaaba1e48cb9b57947b27deac62 |
| Source note | uspto-grants-2006_09 |