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Sodium Carbonate → Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate

HRID 464220
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 464220
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Cl-].[CH:10]([O:23][C:24]([C:26]1[N:31]2[C:32](=[O:48])[CH:33]([NH:34][C:35](=[O:47])[C:36]([C:41]3[N:45]=[C:44]([NH2:46])[S:43][N:42]=3)=[N:37][O:38][CH2:39][CH3:40])[C@H:30]2[S:29][CH2:28][C:27]=1[CH2:49][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(OCC)(=O)C>[NH2:46][C:44]1[S:43][N:42]=[C:41]([C:36](=[N:37][O:38][CH2:39][CH3:40])[C:35]([NH:34][CH:33]2[C:32](=[O:48])[N:31]3[C:26]([C:24]([O:23][CH:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:25])=[C:27]([CH:49]=[CH:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)[CH2:28][S:29][C@H:30]23)=[O:47])[N:45]=1
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Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 131714367[4-Benzhydryloxycarbonyl-7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-cephem-3-ylmethyl]triphenylphosphonium chloride

Produkt 1

HCID 131714369
Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate
Ausbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Nicotinaldehyde (1.1 g) was added to a solution of {4-benzhydryloxycarbonyl-7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-cephem-3-ylmethyl}triphenylphosphonium chloride (syn isomer) (3.0 g) in tetrahydrofuran (30 ml) and water (15 ml) and the solution was adjusted to pH 9.0 with 20% aqueous sodium carbonate. The solution was stirred at ambient temperature for 2 hours under keeping the pH 8.8 to 9.2 with 20% aqueous potassium carbonate. Ethyl acetate and water were added to the resulting solution. The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography using a mixture of acetone and dichloromethane (rate 1:1) as eluent. The eluted fractions were evaporated to give benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (cis-trans mixture) (1.1 g).

Aufarbeitung

  1. washThe separated organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product obtained by concentration
  4. customwas purified by silica gel column chromatography
  5. additiona mixture of acetone and dichloromethane (rate 1:1) as eluent
  6. customThe eluted fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9f082a8ffc664c818261c18cf156682a
Quelldatensatz
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04546101

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