Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 332252Generated: October 29, 2026

Lithium hydroxide, monohydrate → (3-{[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acid

https://huagongshe.com/reaction/332252

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium hydroxide, monohydrateHCID 168937—
Reactant(3-{[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acid ethyl esterHCID 68445346—
CatalystHydrochloric AcidHCID 313—
CatalystMethanolHCID 887—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product(3-{[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acidHCID 5752009784.8%

Reaction Steps

To a solution of (3-{[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-3-carbonyl]-amino}-piperidin-1-yl)-acetic acid ethyl ester (538 mg, 1.1 mmol) in THF (5 mL) was added a solution of lithium hydroxide monohydrate (94 mg, 2.2 mmol) in water (5 mL) and methanol (1 mL) added and the resulting mixture stirred at room temperature overnight. The mixture was acidified to pH 4 with HCl (25%, 3 drops) and methanol (2 drops) added. A gum began to form and the mixture was cooled at 0° C. for 1.5 h and then the aqueous layer decanted off. Trituration with diethylether and hexane afforded the title compound (420 mg, 83%) which was obtained as an off white solid. MS: m/e=449.0 [M−H]−.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08877783B2
Source datasetuspto-grants-2014_11
ORD IDord-b6aef62136844a0b9be9983726fa0dfe
Source noteuspto-grants-2014_11