HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-propyl-1,3-oxazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Butyl 3-bromo-2-oxohexanoate | HCID 87440704 | — |
| Reactant | cis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate | HCID 131730860 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-propyl-1,3-oxazole-4-carboxylate | HCID 131730867 | 74.1% |
Reaction Steps
The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate obtained in Example (103b) (0.95 g, 3.09 mmol), butyl 3-bromo-2-oxohexanoate obtained in Example (116a) (5.1 g, 19.2 mmol), sodium bicarbonate (0.64 g, 7.6 mmol) and THF (20 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 2/3, 1/1, 3/2, 2/1) to obtain 1.02 g of the title compound as a light yellow solid (70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-d575c946151a48aab16b1a096eded5ab |
| Source note | uspto-grants-2013_09 |