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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 750932Generated: October 25, 2026

Ammonium Acetate → (S)-N-{3-[4-(4-(1-Cyano-cyclopropylmethylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

https://huagongshe.com/reaction/750932

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium AcetateHCID 517165—
ReactantCyclopropylacetonitrileHCID 643447—
ReactantN-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 54375226—
SolventTolueneHCID 1140—
Product(S)-N-{3-[4-(4-(1-Cyano-cyclopropylmethylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideHCID 6931210169%

Reaction Steps

The mixture of (S)-N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (2.86 mmol), cyclopropylacetonitrile (5.73 mmol), ammonium acetate (catalytic) in 100 ml of toluene was heated at reflux temperature for 5 to 6 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate water mixture, dried and evaporated to give crude product. The crude product was recrystallized from ethyl acetate to furnish title compound in 69% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07405228B2
Source datasetuspto-grants-2008_07
ORD IDord-9afbb5837de94abc90f0dfb3b34b7efb
Source noteuspto-grants-2008_07