HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Bromoacetyl bromide | HCID 61147 | — |
| Reactant | trimethylsilyl (1E)-2,2,2-trifluoro-N-trimethylsilylethanimidate | HCID 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 acid | HCID 69468538 | — |
| Solvent | Dichloromethane | HCID 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 acid | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06294668B1 |
| Source dataset | uspto-grants-2001_09 |
| ORD ID | ord-d0f3e022672b4ebd91b3492f8433a36a |
| Source note | uspto-grants-2001_09 |