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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1425031Generated: October 25, 2026

Lithium Hydroxide → cis(+/-)-2-{3-(Benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylic acid

https://huagongshe.com/reaction/1425031

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium HydroxideHCID 3939—
ReactantEthyl cis(+/-)-2-{3-(benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylateHCID 86648573—
SolventMethanolHCID 887—
SolventDichloromethaneHCID 6344—
Productcis(+/-)-2-{3-(Benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylic acidHCID 8664857466%

Reaction Conditions

Temperature70 °C

Reaction Steps

Ethyl cis(±)-2-{3-(benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidin-1-yl}-1,3-thiazole-5-carboxylate obtained in Example (90f) (0.25 g, 0.55 mmol) was dissolved in methanol (5 mL) and dichloromethane (1 mL). A 2 N aqueous lithium hydroxide solution (5 mL, 10 mmol) was added, and the mixture was stirred at 70° C. for 20 minutes. The organic solvent was evaporated under reduced pressure, and 1 N hydrochloric acid was added until the pH of the solution was about 4. Purification by reverse phase chromatography (elution solvent: acetonitrile/water=1/1, 4/1) gave 0.15 g of the title compound as a white solid (66%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08927588B2
Source datasetuspto-grants-2015_01
ORD IDord-50d687c45b0f4a5da285cf5746a49e3e
Source noteuspto-grants-2015_01