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

HRID 1597708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597708
[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](/[CH:14]=[C:15]1/[C:16](=[O:28])[N:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[CH2:18][CH2:19]/1)=[C:7]2[C:11]([OH:13])=[O:12].C[Si](/N=C(/O[Si](C)(C)C)\C(F)(F)F)(C)C.[Br:44][CH2:45][C:46](Br)=[O:47].C(OCC)C>ClCCl>[Br:44][CH2:45][C:46]([NH:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](/[CH:14]=[C:15]1/[C:16](=[O:28])[N:17]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)[CH2:18][CH2:19]/1)=[C:7]2[C:11]([OH:13])=[O:12])=[O:47]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 61147Bromoacetyl bromideHCID 5366669trimethylsilyl (1E)-2,2,2-trifluoro-N-trimethylsilylethanimidateHCID 69468538(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

Produkt 1

HCID 69465125(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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  1. filtrationAfter 15 min the solid material was collected by filtration
  2. washwashed with diethyl ether
  3. customdried in high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d0f3e022672b4ebd91b3492f8433a36a
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294668B1

Notizen zur Reaktion

Wird geladen…