HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopentylamine → HCID 68322607, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopentylamine | HCID 2906 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 4-(((1,1-Dimethylethoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid | HCID 2757226 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68322607 | HCID 68322607 | 37.3% |
Reaction Steps
To a stirred suspension of 4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-imidazole-2-carboxylic acid (724 mg, 3.0 mmol) in DMF (6 mL) is added TBTU (1.16 g, 3.6 mmol). After 15 min cyclopentylamine (0.44 mL, 4.5 mmol) is added. After 20 h an additional portion of cyclopentylamine (0.44 mL, 4.5 mmol) is added, and stifling continued for a further 24 h. The mixture is diluted with EtOAc and washed in turn with 1M aqueous NaHSO4, Na2CO3 and brine. The organic layer is dried (MgSO4) and evaporated. The crude material is purified by column chromatography using a gradient of 10-100% EtOAc/heptane to afford the title compound (345 mg, 37%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09073926B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-cea706b253f043e8934d533c34e2b7d5 |
| Source note | uspto-grants-2015_07 |