Acetic Acid → 3-Acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 261976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261976
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:35][C:36]1[S:37][CH:38]=[C:39]([C:41](=[N:45][O:46][CH3:47])[C:42]([OH:44])=O)[N:40]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:48][C:49]([O:51][CH2:52][C:53]1[CH2:62][S:61][C@@H:56]2[C@H:57]([NH2:60])[C:58](=[O:59])[N:55]2[C:54]=1[C:63]([OH:65])=[O:64])=[O:50].C(O)(=O)C>C(Cl)Cl.C(N(CC)CC)C.C(OCC)(=O)C>[C:49]([O:51][CH2:52][C:53]1[CH2:62][S:61][C@@H:56]2[CH:57]([NH:60][C:42](=[O:44])[C:41]([C:39]3[N:40]=[C:36]([NH:35][C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:37][CH:38]=3)=[N:45][O:46][CH3:47])[C:58](=[O:59])[N:55]2[C:54]=1[C:63]([OH:65])=[O:64])(=[O:50])[CH3:48]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 4413287-Aminocephalosporanic acidHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid

Produkt 1

HCID 1317115023-Acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.78 g of dicyclohexylcarbodiimide was added to a solution of the dry acid of Step C in 30 ml of dry methylene chloride and the mixture was stirred for an hour at room temperature and ws then vacuum filtered to remove dicyclohexyl urea formed. The filtrate was cooled to -10° C. and a solution of 1.01 g of 7-amino-cephalosporanic acid in 13 ml of methylene chloride and 0.9 ml of triethylamine was added. The temperature returned to room temperature and 1 ml of acetic acid was added thereto. The mixture was vacuum filtered and the filtrate was washed with aqueous hydrochloric acid, dried and concentrated to dryness. The residue was taken up in 10 ml of dioxane and 1 ml of water and 3 ml of a saturated sodium bicarbonate aqueous solution were added thereto. The mixture was stirred and vacuum filtered and the filtrate was washed and evaporated to dryness. The residue was taken up in methylene chloride and the solution was washed with 10 ml of water and 5 ml of N hydrochloric acid. The mixture was decanted and the organic phase was washed with water, dried and effloresced with ether to obtain 1.747 g of raw product. The latter was dissolved in ethyl acetate and was crystallized by addition of ether to obtain 1.255 g of pure 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]-ceph-3-eme-4-carboxylic acid in the syn configuration.

Aufarbeitung

  1. filtrationws then vacuum filtered
  2. customto remove dicyclohexyl urea
  3. customformed
  4. temperatureThe filtrate was cooled to -10° C.
  5. customreturned to room temperature
  6. filtrationfiltered
  7. washthe filtrate was washed with aqueous hydrochloric acid
  8. customdried
  9. concentrationconcentrated to dryness
  10. addition1 ml of water and 3 ml of a saturated sodium bicarbonate aqueous solution were added
  11. stirringThe mixture was stirred
  12. filtrationvacuum filtered
  13. washthe filtrate was washed
  14. customevaporated to dryness
  15. washthe solution was washed with 10 ml of water and 5 ml of N hydrochloric acid
  16. customThe mixture was decanted
  17. washthe organic phase was washed with water
  18. customdried
  19. customto obtain 1.747 g of raw product
  20. customwas crystallized by addition of ether

Quellen und Nachweise

ORD-Eintrag
ord-8ca57078ca924c93b87422347ab1d997
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152432

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