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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1425114Generated: November 3, 2026

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

https://huagongshe.com/reaction/1425114

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantButyl 3-bromo-2-oxopentanoateHCID 86648534—
Reactantcis(+/-)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamateHCID 131730860—
SolventTetrahydrofuranHCID 8028—
ProductEthyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylateHCID 131730862108.6%

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) (0.98 g, 3.2 mmol), butyl 3-bromo-2-oxopentanoate obtained in Example (110a) (5 g, 19.9 mmol), sodium bicarbonate (0.63 g, 7.5 mmol) and THF (20 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1, 4/1) to obtain 1.5 g of the title compound as a yellow solid (100%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08927588B2
Source datasetuspto-grants-2015_01
ORD IDord-e084d7296c484ac7a597b1c21b6ad5a2
Source noteuspto-grants-2015_01