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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1861230Generated: November 1, 2026

Thiocyanic acid, chloromethyl ester → [4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]sulfanylmethyl thiocyanate

https://huagongshe.com/reaction/1861230

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThiocyanic acid, chloromethyl esterHCID 76755—
Reactant5-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-oneHCID 22966197—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product[4-[(5S)-5-(acetamidomethyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl]sulfanylmethyl thiocyanateHCID 485766—

Reaction Steps

Prepared according to Method B of the General Procedures for Preparation of 5-(S)-(N-Acylaminomethyl)-3-[4′-(substituted)thio-3′-fluorophenyl]oxazolidine-2-ones from 5-(S)-acetamidomethyl-3-[4′-(triphenylmethyl)thio-3′-fluorophenyl]oxazolidine-2-one with chloromethyl thiocyanate (0.041 g, 0.38 mmol) in N-methylpyrrolidine-2-one (1 mL). The synthesis was performed at r.t. for 2 h. The crude product was purified by TLC (eluent: 10% methanol in dichloromethane). Yield 0.022 g (35%). MS (m/z): 324 [M+H]+. 1H NMR.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06531470B1
Source datasetuspto-grants-2003_03
ORD IDord-6d4f719b0e3545e685d512010e902003
Source noteuspto-grants-2003_03