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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 329675Generated: October 29, 2026

Hydrochloric Acid → (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

https://huagongshe.com/reaction/329675

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantPotassium Phosphate, DibasicHCID 24450—
Reactant(3S,4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinoneHCID 14138755—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinoneHCID 1432905989%

Reaction Steps

The keto ester 2 (1.047 g, 2.73 mmol) in methanol (12.3 ml) was treated with 6N HCl (1.37 ml, 8.22 mmol, 3 eg) and stirred 1 hour at room temperature. The solution was treated with 1M K2HPO4 (8.2 ml) and stirred a few minutes, then diluted with ethylacetate and water. The organic layer was separated, washed with 5% NaHCO3 and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to give the product 3 (0.653 g, 89%) as a clear oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04892869
Source datasetuspto-grants-1990_01
ORD IDord-0ae4142789d4493380135c93e84eb8fa
Source noteuspto-grants-1990_01