HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopentylamine → (R)-tert-butyl 1-(cyclopentylamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopentylamine | HCID 2906 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | N-(tert-Butoxycarbonyl)-3-hydroxy-D-valine | HCID 11299247 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-tert-butyl 1-(cyclopentylamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate | HCID 67224582 | 93.2% |
Reaction Steps
To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoic acid (0.5 g, 2.144 mmol), HATU (0.978 g, 2.57 mmol) and cyclopentanamine (0.423 mL, 4.29 mmol) in DCM (10 mL) was added Et3N (0.598 mL, 4.29 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, concentrated, and purified by silica column chromatography (MeOH/DCM, 0-10%) to afford the title compound (0.6 g, 93%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08420816B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-49818e5bc6df4647b489e3bf845653c5 |
| Source note | uspto-grants-2013_04 |