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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2413710Generated: November 1, 2026

Hydrochloric Acid → (2S,3R)-3-azido-4-oxo-2-azetidinecarboxylic acid

https://huagongshe.com/reaction/2413710

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium HydroxideHCID 14798—
Reactant(2S,3R)-1-t-butyldimethylsilyl-3-azido-4-oxo-2-azetidinecarboxylic acidHCID 13712291—
SolventMethanolHCID 887—
SolventDimethylformamideHCID 6228—
Product(2S,3R)-3-azido-4-oxo-2-azetidinecarboxylic acidHCID 13712293—

Reaction Steps

In 39 ml of methanol was dissolved 1.78 g of compound (23) and 9.85 ml of 1N hydrochloric acid was added to the solution. The mixture was stirred for 1.75 hours at room temperature. The reaction mixture was cooled to 0° C. and 9.85 ml of 1N sodium hydroxide was added thereto. The mixture was concentrated to dryness under reduced pressure to obtain an oil. The oil was dissolved in 10 ml of DMF and 3A molecular sieve was added thereto. After the mixture was allowed to stand overnight, the solvent was removed by distillation under reduced pressure to obtain (2S,3R)-3-azido-4-oxo-2-azetidinecarboxylic acid (24). This compound was used in the following Example 7 as it was.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04719207
Source datasetuspto-grants-1988_01
ORD IDord-eef52db0d70043b1a034e928c151ab6a
Source noteuspto-grants-1988_01