Diisopropyl Ether → 7beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate

HRID 1376418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376418
Cl.Cl.Cl.[NH2:4][C@@H:5]1[C:25](=[O:26])[N:7]2[C:8]([C:22]([O-:24])=[O:23])=[C:9]([CH2:12][N+:13]3[N:14]([CH2:19][CH2:20][OH:21])[C:15]([NH2:18])=[CH:16][CH:17]=3)[CH2:10][S:11][C@H:6]12.C[Si](C)(C)NC(=O)C.Cl.[NH2:36][C:37]1[S:41][N:40]=[C:39](/[C:42](=[N:46]/[O:47][CH2:48][CH:49]=[CH2:50])/[C:43](Cl)=[O:44])[N:38]=1.C(OC(C)C)(C)C>O1CCCC1>[NH2:36][C:37]1[S:41][N:40]=[C:39]([C:42](=[N:46][O:47][CH2:48][CH:49]=[CH2:50])[C:43]([NH:4][C@@H:5]2[C:25](=[O:26])[N:7]3[C:8]([C:22]([O-:24])=[O:23])=[C:9]([CH2:12][N+:13]4[N:14]([CH2:19][CH2:20][OH:21])[C:15]([NH2:18])=[CH:16][CH:17]=4)[CH2:10][S:11][C@H:6]23)=[O:44])[N:38]=1

Komponenten

6

Edukt 4

HCID 7914Diisopropyl EtherHCID 25989Acetamide, N-(trimethylsilyl)-HCID 20075415(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-prop-2-enoxyiminoacetyl chloride;hydrochlorideHCID 1317165287beta-Amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate trihydrochloride

Produkt 1

HCID 1317179017beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylateAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7β-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate trihydrochloride (2 g) and N-(trimethylsilyl)acetamide (5.85 g) in tetrahydrofuran (40 ml)was added (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetyl chloride hydrochloride (1.26 g) under ice-cooling. After being stirred for 1 hour at the same temperature, the reaction mixture was poured into diisopropyl ether (200 ml). The resulting precipitate was collected by filtration, dissolved in water (100 ml) and adjusted to pH 2.0 with 5% sodium bicarbonate solution. This solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries). The desired compound was eluted with 10% isopropyl alcohol and lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer) (1.07 g).

Aufarbeitung

  1. temperaturecooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutiondissolved in water (100 ml)
  4. custom" (Trademark: prepared by Mitsubishi Chemical Industries)
  5. washThe desired compound was eluted with 10% isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-d64a8f4a4efb4e239a1fe2a888924ce5
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663163

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