HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → ((1,1-Dimethylethyl)oxymethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | Methyl 2-(bromomethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate | HCID 57705537 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | ((1,1-Dimethylethyl)oxymethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylic acid | HCID 57705535 | 20% |
Reaction Steps
A mixture of T39.2 (0.245 g, 0.69 mmol) and sodium 2-methylpropan-2-olate (0.20 g, 2.1 mmol) in DMF (6 mL) was stirred at room temperature for 28 minutes. The mixture was acidified with 1N HCl to pH 3-4 and then was extracted with EtOAc (100 mL). The organic phase was washed with brine and dried over anhydrous Na2SO4. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:4 EtOAc/hexane) and gave T39.3 (49 mg) in 20% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748462B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-0af8127605f44c5e80c75cf44e7cf529 |
| Source note | uspto-grants-2014_06 |