HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → N-{(1S)-2-[4-(6-hydroxy-1,3-benzoxazol-2-yl)phenoxy]-1-methylethyl}acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | 4-{[(2S)-2-(acetylamino)propyl]oxy}-N-(2,4-dihydroxyphenyl)benzamide | HCID 67777722 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-{(1S)-2-[4-(6-hydroxy-1,3-benzoxazol-2-yl)phenoxy]-1-methylethyl}acetamide | HCID 67778241 | 54.8% |
Reaction Steps
To a solution of 4-{[(2S)-2-(acetylamino)propyl]oxy}-N-(2,4-dihydroxyphenyl)benzamide (628 mg) and triphenylphosphine (716 mg) in THF (6.0 mL) was added dropwise a toluene solution (2.2 M, 1.24 mL) of diethyl azodicarboxylate, and the mixture was stirred under a nitrogen atmosphere at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (326 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08729102B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-cd8eaaa16e78452d9da037cfee17ba4b |
| Source note | uspto-grants-2014_05 |