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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1425148Generated: November 1, 2026

Sodium Bicarbonate → Ethyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-propyl-1,3-oxazole-4-carboxylate

https://huagongshe.com/reaction/1425148

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantButyl 3-bromo-2-oxohexanoateHCID 87440704—
Reactantcis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamateHCID 131730860—
SolventTetrahydrofuranHCID 8028—
ProductEthyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-propyl-1,3-oxazole-4-carboxylateHCID 13173086774.1%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08927588B2
Source datasetuspto-grants-2015_01
ORD IDord-b22e2df9c27741c8b926ecb654acc924
Source noteuspto-grants-2015_01