HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tert-butyl 2,2,2-trichloroethanimidate → tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-hydroxypropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tert-butyl 2,2,2-trichloroethanimidate | HCID 2734700 | — |
| Reactant | (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoic acid | HCID 6541433 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-hydroxypropanoate | HCID 13965220 | 68.3% |
Reaction Steps
To a solution of commercial N-Fmoc-L-serine (1.5 g, 4.58 mmol) in EtOAc (40 ml), a solution of t-butyl 2,2,2-trichloroacetimidate (4.00 g, 18.32 mmol) in cyclohexane (18 ml) was added dropwise. After stirring at room temperature for 24 hrs, the solution was evaporated and the residue was purified by flash chromatography (n-Hexane/EtOAc 70:3), yielding the title compound (1.20 g, 68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09266820B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-28932fd93c5d4c7dbdb19f8ffbd9edea |
| Source note | uspto-grants-2016_02 |