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Sodium Chloride → 7beta-(t-Butoxycarbonyl)amino-3-[2-(N-tosylcarbamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid

HRID 261716
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 261716
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:21](=[O:22])[N:11]2[C:12]([C:18]([O-:20])=[O:19])=[C:13]([CH2:16][OH:17])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].C(N(CC)CC)C.[S:31]([N:41]1[C:45](=[O:46])[C:44]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:43]2[C:42]1=[O:51])([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32].[Cl-].[Na+]>CN(C)C=O.O.C(OCC)(=O)C.C(O)(=O)C.CCCCCC.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:21](=[O:22])[N:11]2[C:12]([C:18]([OH:20])=[O:19])=[C:13]([CH2:16][O:17][C:45](=[O:46])[C:44]3[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=3[C:42](=[O:51])[NH:41][S:31]([C:34]3[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

11

Edukt 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 2141332-((4-Methylphenyl)sulfonyl)-1H-isoindole-1,3(2H)-dioneHCID 70582610Sodium 7beta-(t-butoxycarbonyl)amino-3-hydroxymethyl-3-cephem-4-carboxylate

Produkt 1

HCID 705836227beta-(t-Butoxycarbonyl)amino-3-[2-(N-tosylcarbamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid
Ausbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In N,N-dimethylformamide (8 ml), is dissolved sodium 7β-(t-butoxycarbonyl)amino-3-hydroxymethyl-3-cephem-4-carboxylate (1.60 g), followed by addition of triethylamine (3 ml) and N-tosylphthalimide (1.80 g) under ice-cooling. The mixture is stirred for one hour and then poured into toluene (300 ml). n-Hexane (200 ml) is added and the resultant precipitate is collected by filtration, washed with toluene and dried. The powder thus obtained is dissolved in water (50 ml). The solution is adjusted to pH 3.7 with acetic acid and a saturated aqueous solution of sodium chloride (50 ml) is added. The resultant precipitate is collected by filtration and washed with water. The cake thus obtained is added to a mixed solution of ethyl acetate (30 ml) and water (10 ml). After separation, the ethyl acetate layer is washed with water and water (10 ml) is added. Sodium hydrogen carbonate is added to adjust to pH 6.8. After separation, the aqueous layer is washed with ethyl acetate and ethyl acetate (20 ml) is added. To the mixture, diluted phosphoric acid is added to adjust to pH 4.0. After separation, the ethyl acetate layer is washed with water, dried over anhydrous sodium sulfate and concentrated. To the residue, ether is added under stirring and the resultant insolubles are filtered off. The filtrate is concentrated under reduced pressure and carbon tetrachloride is added. The resultant precipitate is collected by filtration and dried over phosphorous pentoxide. The procedure provides 7β-(t-butoxycarbonyl)amino-3-[2-(N-tosylcarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (1.21 g).

Aufarbeitung

  1. temperaturecooling
  2. filtrationthe resultant precipitate is collected by filtration
  3. washwashed with toluene
  4. customdried
  5. customThe powder thus obtained
  6. filtrationThe resultant precipitate is collected by filtration
  7. washwashed with water
  8. customThe cake thus obtained
  9. customAfter separation
  10. washthe ethyl acetate layer is washed with water and water (10 ml)
  11. additionis added
  12. additionSodium hydrogen carbonate is added
  13. customAfter separation
  14. washthe aqueous layer is washed with ethyl acetate and ethyl acetate (20 ml)
  15. additionis added
  16. additionTo the mixture, diluted phosphoric acid is added
  17. customAfter separation
  18. washthe ethyl acetate layer is washed with water
  19. dry with materialdried over anhydrous sodium sulfate
  20. concentrationconcentrated
  21. additionTo the residue, ether is added
  22. stirringunder stirring
  23. filtrationthe resultant insolubles are filtered off
  24. concentrationThe filtrate is concentrated under reduced pressure and carbon tetrachloride
  25. additionis added
  26. filtrationThe resultant precipitate is collected by filtration
  27. dry with materialdried over phosphorous pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-f0f5e5cb5d7249b1ba26935217877f3b
Quelldatensatz
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04166178

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