HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl 3-(5-(benzyloxy)-2-((1E)-3-(benzyloxy)-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate → 3-(2-(5-(tert-Butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl 3-(5-(benzyloxy)-2-((1E)-3-(benzyloxy)-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | HCID 118292836 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(2-(5-(tert-Butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acid | HCID 118292812 | 114.9% |
Reaction Steps
A mixture of tert-butyl 3-(5-(benzyloxy)-2-((1E)-3-(benzyloxy)-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (260 mg), 10% Pd/C (containing about 55% water, 26 mg), and THF (3 mL) was stirred overnight at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was combined with 10% Pd/C (containing about 55% water, 52 mg) and THF (3 mL), and the obtained mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure to obtain the title compound (214 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428470B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-add145f999aa4f798bc1cd4eae137254 |
| Source note | uspto-grants-2016_08 |