HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → tert-Butyl 2-(5-formylthiophene-2-carboxamido)phenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | N-(tert-Butoxycarbonyl)-1,2-phenylenediamine | HCID 676311 | — |
| Reactant | 5-Formyl-2-thiophenecarboxylic Acid | HCID 818882 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 2-(5-formylthiophene-2-carboxamido)phenylcarbamate | HCID 58930645 | 33.5% |
Reaction Steps
A solution of 5-formylthiophene-2-carboxylic acid (350 mg, 2.24 mmol), tert-butyl 2-aminophenylcarbamate (467 mg, 2.24 mmol) and triethylamine (470 μL, 340 mg, 3.36 mmol) and BOP (1.1 g, 2.68 mmol) in DMF (10 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated and purified by flash chromatography using 25% EtOAc in hexanes as an eluent, yielding 260 mg (33%) of the title compound. 1H NMR (CDCl3) 9.95 (s, 1H), 9.7 (br. s, 1H), 7.84 (d, 1H, J=8.0 Hz), 7.74 (m, 2H), 7.15 (m, 2H), 6.72 (s, 1H), 1.56 (s, 9H). LRMS: (calc) 346.1; (found) 369.1 (M+Na)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08088805B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-ee460b9b649d4ae1a10c3f119c93cbb9 |
| Source note | uspto-grants-2012_01 |