HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 3-(2-Aminoethyl)phenol hydrochloride | HCID 77001 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 5-(Methoxycarbonyl)-4-methylthiophene-2-carboxylic acid | HCID 68226619 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester | HCID 68226703 | 162.8% |
Reaction Steps
To a solution of 3-methyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (0.1 g, 0.5 mmol) and 3-hydroxyphenethylamine hydrochloride (105 mg, 0.6 mmol) in DMF (5 ml) was added at rt triethylamine (0.21 ml, 1.5 mmol), HOBT (81 mg, 0.6 mmol) and HBTU (230 mg, 0.6 mmol). The mixture was stirred at rt for 1 h, then quenched with 1NHCl and extracted with EtOAc. The layers were separated. The organic layer was washed with brine, then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 15-65% EtOAc in hexane to afford the desired product (260 mg, 81% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404859B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-e8c500d4454340d7bce6129625354ae3 |
| Source note | uspto-grants-2013_03 |