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Hydrochloric Acid → 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255769
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 255769
P(Cl)(Cl)(Cl)=O.[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][C:21](=O)[NH2:22])[C:15]([OH:17])=O)[N:13]=1)=[O:7].[NH2:24][CH:25]1[C:43](=[O:44])[N:27]2[C:28]([C:40]([OH:42])=[O:41])=[C:29]([CH2:32][S:33][C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)[CH2:30][S:31][C@H:26]12.Cl>O1CCCC1.CC(C)=O.C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][C:21]#[N:22])[C:15]([NH:24][CH:25]2[C:43](=[O:44])[N:27]3[C:28]([C:40]([OH:42])=[O:41])=[C:29]([CH2:32][S:33][C:34]4[N:38]([CH3:39])[N:37]=[N:36][N:35]=4)[CH2:30][S:31][C@H:26]23)=[O:17])[N:13]=1)=[O:7]
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Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 538052302-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid

Produkt 1

HCID 1317152977-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid
Ausbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of phosphoryl chloride (3.68 g.), N,N-dimethylformamide (1.75 g.) and tetrahydrofuran (4 ml.) was stirred at -5° to -10° C. for 30 minutes and added to a suspension of 2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 2 g.) in tetrahydrofuran (16 ml.). The mixture was stirred at the same temperature to give an activated acid solution. On the other hand, a suspension of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (3.62 g.) in 50% aqueous acetone (36 ml.) was adjusted to pH 7.5 with triethylamine. The activated acid solution was added dropwise to the above solution at 0° to -5° C. while keeping at pH 7.5 to 8.0 with triethylamine and stirred at the same temperature for 30 minutes. Ethyl acetate (100 ml.) was added to the resultant solution and adjusted to pH 2.5 with 10% hydrochloric acid. After filtration, the filtrate was extracted with ethyl acetate (100 ml.) twice. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether and the precipitates were collected by filtration to give 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.12 g.).

Aufarbeitung

  1. customto give an activated acid solution
  2. additionThe activated acid solution was added dropwise to the above solution at 0° to -5° C.
  3. stirringstirred at the same temperature for 30 minutes
  4. filtrationAfter filtration
  5. extractionthe filtrate was extracted with ethyl acetate (100 ml.) twice
  6. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diethyl ether
  10. filtrationthe precipitates were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-f6192a7925494e8590638fcf7d5e8747
Quelldatensatz
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04698337

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