HuagongsheHuagongshe Chemistry Print Report · For research reference only
Fenbufen → N-(4-azidobutyl)-4-(biphenyl-4-yl)-4-oxobutanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Fenbufen | HCID 3335 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Butanamine, 4-azido- | HCID 150111 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetone hexane | HCID 21880519 | — |
| Product | N-(4-azidobutyl)-4-(biphenyl-4-yl)-4-oxobutanamide | HCID 58554685 | 77% |
Reaction Steps
A solution of fenbufen (214 mg, 0.8 mmol), HBTU (302 mg, 0.8 mmol), DIEA (1 mL, 0.8 mmol) and DMF (15 mL) was stirred. 4-azido-1-butanamine was added. TLC (acetone/n-hexane= 3/7) indicated the consumption of starting material (Rf=0.39) and the formation of the product (Rf=0.78). After stirring for 1 hr, the mixture was concentrated under high vacuum at 60° C. The residue was purified by flash chromatography using acetone: n-hexane=3:7 as eluents to provide a snow-white solid in 77% yield (269 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08093427B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-98b1634e93a64cb8be46531ac5ff23ad |
| Source note | uspto-grants-2012_01 |