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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1597708Generated: October 30, 2026

Diethyl Ether → (E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

https://huagongshe.com/reaction/1597708

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantBromoacetyl bromideHCID 61147—
Reactanttrimethylsilyl (1E)-2,2,2-trifluoro-N-trimethylsilylethanimidateHCID 5366669—
Reactant(E)-(6R,7R)-7-amino-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 69468538—
SolventDichloromethaneHCID 6344—
Product(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 69465125—

Reaction Steps

(E)-(6R,7R)-7-amino-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (736.0 mg, 1.83 mmol) was suspended in 20 ml dichloromethane and N,O-bis(trimethylsilyl)-trifluoroacetamide (1.94 ml, 7.32 mmol) was added. After 45 min bromoacetyl bromide (167 ml, 1.92 mmol) was added dropwise. After 1 h the reaction mixture was poured on 200 ml diethyl ether containing 160 ml water. After 15 min the solid material was collected by filtration, washed with diethyl ether and dried in high vacuum.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06294668B1
Source datasetuspto-grants-2001_09
ORD IDord-d0f3e022672b4ebd91b3492f8433a36a
Source noteuspto-grants-2001_09