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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 393398Generated: October 27, 2026

Citric Acid → HCID 10965692, compound

https://huagongshe.com/reaction/393398

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
Reactant(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneHCID 9903372—
SolventEthanolHCID 702—
ProductHCID 10965692HCID 1096569280%

Reaction Conditions

Temperature70 °C

Reaction Steps

To (2S,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane obtained in the same manner as in Reference Example 2 (2.75 g) was added ethanol (27.5 ml). 6.8% Aqueous citric acid solution (29.5 g) was then added thereto, and the mixture was stirred at 70° C. for 2 hr. After cooling to room temperature, ethanol was removed under reduced pressure. The residue was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Further, a mixed solvent of hexane (2.5 ml) and ethyl acetate (2.5 ml) was added to allow precipitation of the crystals. The crystals were collected by filtration and washed twice with a mixed solvent of hexane/ethyl acetate (1/1). The obtained crystals were dried to give the objective (4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one (1.79 g) in a yield of 80%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06806384B2
Source datasetuspto-grants-2004_10
ORD IDord-ff46a0c381984ace95102ac73e0a5840
Source noteuspto-grants-2004_10