HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → tert-Butyl 3-(3-(benzyloxy)-5-((1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl acrylate | HCID 15458 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | tert-Butyl 3-(3-(benzyloxy)-5-bromophenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | HCID 118292799 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 3-(3-(benzyloxy)-5-((1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | HCID 118292792 | 50.1% |
Reaction Steps
A mixture of tert-butyl 3-(3-(benzyloxy)-5-bromophenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (500 mg), tert-butyl acrylate (586 mg), palladium acetate (10.27 mg), tris(2-methylphenyl)phosphine (41.8 mg), triethylamine (0.383 mL), and DMF (5 mL) was stirred at 100 C for 2 days under an argon atmosphere. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (272 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428470B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-5b55baae129a4309aa996b56357939e1 |
| Source note | uspto-grants-2016_08 |