Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethynyl-4-methoxybenzene | HCID 251020 | — |
| Reactant | Sulfamyl iodide | HCID 18761200 | — |
| Reactant | HCID 86756488 | HCID 86756488 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86756487 | HCID 86756487 | — |
Reaction Steps
Methyl 2-[4-(4-Methoxyphenyl)-acetylenylbenzenesulfonyl]-amino-5-phenylpent-4-ynoate: The starting iodo sulfonamide 3a (0.54 g, 1.15 mmol) and 4-methoxyphenylacetylene (0.2 g, 1.49 mmol) are taken in 10 mL of DMF in the presence of 0.32 mL of Et3N, Pd(PPh3)2Cl2 (40.4 mg, 0.058 mmol), and CuI (24 mg, 0.128 mmol). The mixture is then heated to 55° C. for 18 hr. and then partitioned between EtOAc and H2O. The organic layer is washed with 1N HCl, aqueous NaHCO3 and brine, dried over MgSO4, filtered and evaporated to give a residue which is adsorbed onto silica and eluted through a column of flash silica with hexane:EtOAc (4:1 to 2:1 ) to give the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06197770B1 |
|---|
| Source dataset | uspto-grants-2001_03 |
|---|
| ORD ID | ord-a0ae5461681d451e943528a3e4532856 |
|---|
| Source note | uspto-grants-2001_03 |
|---|
