HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-phenyl-thiophene-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenemethanamine | HCID 22266169 | — |
| Reactant | 5-(Methoxycarbonyl)-4-phenylthiophene-2-carboxylic acid | HCID 58121085 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-phenyl-thiophene-2-carboxylic acid methyl ester | HCID 68226964 | 39.1% |
Reaction Steps
To a solution of 3-Phenyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (500 mg, 1.91 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.53 mL, 3.82 mmol), HBTU (1.45 g, 3.82 mmol), HOBT (390 mg, 3.82 mmol), and 3-(tert-Butyl-dimethyl-silanyloxy)-benzylamine (540 mg, 2.29 mmol). The mixture was stirred at room temperature 1 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-30% EtOAc in hexane to afford the desired product (0.36 g, 39% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08404859B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-d270c2a0fa4347b0b2c0f74e9a0ffde8 |
| Source note | uspto-grants-2013_03 |