HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 67235543, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | HCID 67236248 | HCID 67236248 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67235543 | HCID 67235543 | 16% |
Reaction Steps
To a solution of the crude 1-(3-Amino-3-methylbutyl)-1H-indole-2,6-dicarboxylic acid from the preceding step in THF (9.0 mL) is added 1,1′-carbonyldiimidazole (162 mg, 0.90 mmol) followed by 1,8-diazabicyclo[5.4.0] undec-7-ene (0.14 mL, 0.90 mmol). The mixture is stirred at room temperature for 2 h. Acetic acid (0.3 mL) and water (50 mL) are added and the mixture is extracted with EtOAc. The organic layers are dried (Na2SO4) and concentrated. The crude compound is purified by flash column chromatography using 10% methanol in CH2Cl2 to afford the title compound (17 mg, 16% for three steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150577B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-40aed164b44848e89c1c5bfeaf33580b |
| Source note | uspto-grants-2015_10 |