HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)-5-methyl-1,3-oxazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Butyl 3-bromo-2-oxobutanoate | HCID 87440690 | — |
| Reactant | HCID 131730866 | HCID 131730866 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)-5-methyl-1,3-oxazole-4-carboxylate | HCID 86648609 | 86.6% |
Reaction Steps
The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-propoxypiperidin-4-yl)carbamate obtained in Example (113f) (0.80 g, 2.39 mmol), butyl 3-bromo-2-oxobutanoate obtained in Example (106a) (4 g, 16.9 mmol), sodium bicarbonate (0.7 g, 8.33 mmol) and THF (15 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1) to obtain 0.98 g of the title compound as a light brown oily substance (98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-b878274a3732498c8bfc52d081a5acda |
| Source note | uspto-grants-2013_09 |