HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (2{(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | N-(tert-Butoxycarbonyl)-1,2-phenylenediamine | HCID 676311 | — |
| Reactant | (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid | HCID 68526317 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | (2{(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester | HCID 86621709 | — |
Reaction Steps
A mixture of 5.4 g (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 300 ml DMF and 2.34 g HOBt.H2O and 21.0 ml Triethylamine is stirred at ambient temperature for 0.5 h. Then it is added 8.8 g EDC.HCL and it is stirred again at ambient temperature for 0.5 h. Finally 3.2 g (2-amino-phenyl)-carbamic acid tert-butyl ester are added and the suspension is stirred at ambient temperature for 24 h. The DMF is evaporated and the residue is extracted with ethyl acetate and water. The organic layer is dried over sodium sulfate. The title product is isolated by flash chromatography. By this method 6.3 g of a yellow foam is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815855B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-31b3a8a2e9ce4a21ad2105cf3783a08e |
| Source note | uspto-grants-2014_08 |