HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → 1-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Benzyl azide | HCID 12152 | — |
| Reactant | Sodium Ascorbate | HCID 23667548 | — |
| Reactant | 1-{4'-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester | HCID 86697091 | — |
| Catalyst | Copper Sulfate | HCID 24462 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Water ethylacetate | HCID 22728543 | — |
| Product | 1-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester | HCID 67959649 | — |
Reaction Steps
1-{4′-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.17 g, 0.45 mmol) and benzyl azide (0.072 g, 0.54 mmol) were combined DMSO (5 mL). Copper(II) sulfate (0.001 g, 0.005 mmol) and sodium ascorbate (0.001 g, 0.05 mmol) were combined in H2O (2 mL) and the solution was added to the DMSO mixture. The reaction was stirred at room temperature for 18 hours then submitted to EtOAc/H2O workup. Purification on silica gel (0-70% EtOAc in hexanes) provided the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09272990B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-b503df4c22b2428b84c04444e54d3af1 |
| Source note | uspto-grants-2016_03 |