HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Benzyloxyphenylacetic acid → 4-Benzyloxy-N-methoxy-N-methylphenylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Benzyloxyphenylacetic acid | HCID 81033 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-Benzyloxy-N-methoxy-N-methylphenylacetamide | HCID 11254648 | — |
Reaction Steps
To a stirred solution of (4-benzyloxy-phenyl)-acetic acid (61.9 mmol, 15.0 g), HBTU (74.3 mmol, 28.1 g), and N,O-dimethylhydroxylamine hydrochloride (92.9 mmol, 9.0 g) in DMF (100 mL) at 0° C. was added DIEA (136.3 mmol, 17.5 g) drop-wise. The reaction mixture was warmed to room temperature and stirred for 30 min. The mixture was diluted with ethyl acetate, washed with water, and 1.0 N HCl, followed by brine. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to provide 2-(4-benzyloxy-phenyl)-N-methoxy-N-methyl-acetamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431575B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-71b2bba676b443f5966cc6b612f92f5b |
| Source note | uspto-grants-2013_04 |