HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-tert-butyl 3,3-dimethyl-2-(((S)-tetrahydrofuran-3-yloxy)carbonylamino)butanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl Ester | HCID 11229944 | — |
| Reactant | tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochloride | HCID 56776989 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (S)-tert-butyl 3,3-dimethyl-2-(((S)-tetrahydrofuran-3-yloxy)carbonylamino)butanoate | HCID 59540266 | 55.1% |
Reaction Steps
A mixture of (S)-tert-butyl 2-amino-3,3-dimethylbutanoate hydrochloride (0.05 g, 0.223 mmol), (S)-2,5-dioxopyrrolidin-1-yl tetrahydrofuran-3-yl carbonate (0.056 g, 0.246 mmol) and Hunig's base (0.078 mL, 0.447 mmol) in THF (2.25 mL) was stirred at room temperature for 12 hours. The solvent was evaporated and the product was purified by chromatography on silica gel eluting with 0-15% ethyl acetate in dichloromethane to give the title compound (0.037 g, 55% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278922B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-540acb1c069d4c96ba4b0b5d2d885e1a |
| Source note | uspto-grants-2016_03 |