HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (6-Methoxy-4-oxo-7-(piperidin-4-ylmethoxy)quinazolin-3(4H)-yl)methyl pivalate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl 4-(((6-methoxy-4-oxo-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylate | HCID 11733854 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (6-Methoxy-4-oxo-7-(piperidin-4-ylmethoxy)quinazolin-3(4H)-yl)methyl pivalate | HCID 11058522 | 92% |
Reaction Steps
A solution of 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.32 g, 4.6 mmol) in methylene chloride (23 ml) containing TFA (5 ml) was stirred at ambient temperature for 1 hour. The volatiles were removed under vacuum. The residue was partitioned between ethyl acetate and sodium hydrogen carbonate. The organic solvent was removed under vacuum and the residue was filtered. The precipitate was washed with water, and dried under vacuum. The solid was azeotroped with toluene and dried under vacuum to give 6-methoxy-7-(piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.7 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09040548B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-dfea5019c8a243d3a3521699b66565a1 |
| Source note | uspto-grants-2015_05 |