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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2398956Generated: November 2, 2026

Dimethylformamide → 3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl ester

https://huagongshe.com/reaction/2398956

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant3-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 13729—
ReactantChloromethyl propionateHCID 221144—
ReactantSodiumHCID 5360545—
SolventEthyl AcetateHCID 8857—
Product3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl esterHCID 21425995—

Reaction Steps

To 35 ml of dimethyl formamide is added 7.5 g of the sodium salt of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, and the solution is stirred at room temperature for about 30 minutes after which 8 ml of chloromethylpropionate is added. Stirring is continued at room temperature for about 3 hours. The mixture is dilutedwith ethyl acetate and washed with water. The organic layer is separated and evaporated to dryness. The residue is recrystallized from ethyl acetate to give 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl ester.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04026887
Source datasetuspto-grants-1977_05
ORD IDord-d1811a46625f41c5bb78a4bb58b9a1fa
Source noteuspto-grants-1977_05