HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → HCID 67234992, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1H-Indole-2,6-dicarboxylic acid, 1-[(1S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-methylpropyl]-, 2,6-diethyl ester | HCID 67235550 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67234992 | HCID 67234992 | 46% |
Reaction Steps
To a solution of diethyl 1-{(2S)-4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate (891 mg, 2.1 mmol) in CH2Cl2 (4 mL) is added TFA (3 mL). The mixture is stirred at room temperature for 1 h then the solvent is evaporated. To a solution of the residue in ethanol (10 mL) is added K2CO3 (854 mg, 6.2 mmol). The reaction mixture is refluxed for 4 h with vigorous stifling. EtOAc is added and the organic layer is washed with water, brine, dried (MgSO4) and concentrated to afford crude compound which is purified by flash column chromatography using EtOAc in hexanes then methanol in CH2Cl2 to afford the title compound (269 mg, 46%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150577B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-bac733a44370436a825fa64c10f3c4ff |
| Source note | uspto-grants-2015_10 |