Ethyl Acetate → HCID 178418679, Verbindung

HRID 1734272

Reaktionsgleichung

Reaktionsgleichung von HRID 1734272
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[C:14]([OH:16])[C:13]([OH:17])=[CH:12][N:11]=2)=[O:9])[CH2:4][CH2:3]1.C(C(CCCC)C([O-])=O)C.[Na+].FC(F)(F)C(O)=O.[NH2:36][C:37]1[S:41][N:40]=[C:39]([C:42](=[N:60][O:61][CH2:62][CH:63]=[CH2:64])[C:43]([NH:45][C@@H:46]2[C:58](=[O:59])[N:48]3[C:49]([C:55]([OH:57])=[O:56])=[C:50]([CH2:53]Cl)[CH2:51][S:52][C@H:47]23)=[O:44])[N:38]=1.C(OCC)(=O)C>CS(C)=O>[NH2:36][C:37]1[S:41][N:40]=[C:39]([C:42](=[N:60][O:61][CH2:62][CH:63]=[CH2:64])[C:43]([NH:45][C@@H:46]2[C:58](=[O:59])[N:48]3[C:49]([C:55]([O-:57])=[O:56])=[C:50]([CH2:53][N+:2]4([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([C:10]5[CH:15]=[C:14]([OH:16])[C:13]([OH:17])=[CH:12][N:11]=5)=[O:9])[CH2:4][CH2:3]4)[CH2:51][S:52][C@H:47]23)=[O:44])[N:38]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 23672331Sodium 2-ethylhexanoateHCID 1317181447beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate trifluoroacetateHCID 178418632HCID 178418632, Verbindung

Produkt 1

HCID 178418679HCID 178418679, VerbindungAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

To a suspension of 1-methyl-4-(4,5-dihydroxy-2-pyridylcarbonyl)piperazine (800 mg) in dimethyl sulfoxide (8 ml) was added sodium 2-ethylhexanoate (840 mg). The solution was added dropwise to a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (965 mg) in dimethyl sulfoxide (7 ml) at room temperature. After being stirred for 4 hours, the mixture was poured into ethyl acetate (200 ml) and the resulting precipitates were collected by filtration. The precipitates were dissolved in water and then adjusted to pH 3.0 with aqueous sodium bicarbonate. The resulting solution was subjected to column chromatography on Diaion HP-20 using 15% aqueous isopropyl alcohol as an eluent and the objective fraction was 10 lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[1-methyl-4-(4,5-dihydroxy-2-pyridylcarbonyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (380 mg).

Aufarbeitung

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe precipitates were dissolved in water

Quellen und Nachweise

ORD-Eintrag
ord-c0506454be214ed4ad5b6dd599f607fe
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05532354

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