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Sodium Carbonate → 7-[2-(2-Formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 745413
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 745413
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16](=O)[NH2:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:24][CH:25]1[C:35](=[O:36])[N:27]2[C:28]([C:32]([OH:34])=[O:33])=[CH:29][CH2:30][S:31][C@H:26]12.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.CC(C)=O.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]#[N:17])[C:10]([NH:24][CH:25]2[C:35](=[O:36])[N:27]3[C:28]([C:32]([OH:34])=[O:33])=[CH:29][CH2:30][S:31][C@H:26]23)=[O:12])[N:8]=1)=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 538052302-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid

Produkt 1

HCID 1317123307-[2-(2-Formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-cephem-4-carboxylic acid
Ausbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 1.2 g.), N,N-dimethylformamide (0.768 g.), phosphoryl chloride (1.61 g.) and tetrahydrofuran (2.4 ml.) were treated in a similar manner to that of Example 1-(1) to give an activated acid solution. A suspension of 7-amino-3-cephem-4-carboxylic acid (0.89 g.) in a mixture of tetrahydrofuran (8.9 ml.), acetone (4.5 ml.) and water (4.5 ml.) was adjusted to pH 7 to 8 with 20% aqueous sodium carbonate. The activated acid solution was added to the solution at -5° to 0° C. while keeping at pH 7 to 8 and stirred at the same temperature for 30 minutes. The resultant solution was concentrated in vacuo, and water and ethyl acetate were added to the residue. The solution was adjusted to pH 2.5 and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was pulverized with diethyl ether, collected by filtration and dried to give 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.95 g).

Aufarbeitung

  1. customto give an activated acid solution
  2. additionThe activated acid solution was added to the solution at -5° to 0° C.
  3. concentrationThe resultant solution was concentrated in vacuo, and water and ethyl acetate
  4. additionwere added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. filtrationcollected by filtration
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-319527bb9561427c9315450b2012e40d
Quelldatensatz
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04598147

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