HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-(2-tert-Butoxycarbonylamino-ethoxy)-4-cyano-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl N-(2-bromoethyl)carbamate | HCID 4103526 | — |
| Reactant | Methyl 4-cyano-3-hydroxybenzoate | HCID 16641129 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(2-tert-Butoxycarbonylamino-ethoxy)-4-cyano-benzoic acid methyl ester | HCID 54091503 | — |
Reaction Steps
(2-Bromoethyl)carbamic acid tert-butyl ester (700 mg, 3.12 mmol) from step 1 and 4-cyano-3-hydroxybenzoic acid methyl ester (Example 34 Step 3, 550 mg, 3.12 mmol) was dissolved in DMF (4.5 ml). Cs2CO3 (2.03 g, 6.24 mmol) was added and the reaction stirred at room temperature for 2 hours. The reaction mixture was filtered through celite and washed with DMF (3×10 mL). The DMF was removed in vacuo. The residue was purified by flash chromatography (12% EtOAc/Hexane) to yield the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05939439 |
| Source dataset | uspto-grants-1999_08 |
| ORD ID | ord-f89fbb0ad19a49359fd177b4640d0f7e |
| Source note | uspto-grants-1999_08 |