HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 3-[[2-Fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl 3-[[2-fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoate | HCID 86707317 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-[[2-Fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoic acid | HCID 86707318 | 36.8% |
Reaction Steps
A solution of NaOH (0.146 mg, 0.00366 mol) in 1.5 ml of H2O is added to a stirred solution of methyl 3-[[2-fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoate (0.38 g, 0.000916 mol) in THF:EtOH (3 ml:2 ml). After 4 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with 1N HCl, and extracted with ethyl acetate. The organic layer are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as a light yellow solid (85 mg g, 36.8%). Mass spectrum (m/z): 401.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642768B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-94f070f1972845448fdf4d667aec139f |
| Source note | uspto-grants-2014_02 |