Dichloromethane → 3-Methylthiomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 5156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5156
[CH3:1][S:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH2:15])[C:13](=[O:16])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11].C(Cl)Cl.[C:20]([NH:39][C:40]1[S:41][CH:42]=[C:43]([C:45](=[N:49][O:50][CH3:51])[C:46](O)=[O:47])[N:44]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C.C(N(CC)CC)C.CC(C)=O>[CH3:1][S:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[CH:14]([NH:15][C:46](=[O:47])[C:45]([C:43]3[N:44]=[C:40]([NH:39][C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[S:41][CH:42]=3)=[N:49][O:50][CH3:51])[C:13](=[O:16])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11]

Komponenten

7

Edukt 3

HCID 6344DichloromethaneHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 677128833-Methylthiomethyl-7-amino-ceph-3-eme-4-carboxylic acid

Produkt 1

HCID 1317167853-Methylthiomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 180AcetoneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 2.6 g of 3-methylthiomethyl-7-amino-ceph -3-eme-4-carboxylic acid, 26 ml of methylene chloride and 3 ml of triethylamine was stirred at 20° C. under an inert atmosphere and after cooling the mixture to -20° C., an acetone suspension of the mixed anhydride of Example 3 prepared from 6 g of the triethylamine salt of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetic acid was added thereto. The mixture was stirred for 2 hours at 0° C. and was then acidified with 1 ml of acetic acid. The mixture was evaporated to dryness under reduced pressure and the residue was taken up in 50 ml of methylene chloride. The organic solution was washed with water, dried and evaporated to dryness under reduced pressure. The residue was taken up in 50 ml of ether and the mixture was vacuum filtered to obtain 8.06 g of syn isomer of 3-methylthiomethyl-7-[2-(2 -tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Aufarbeitung

  1. temperatureafter cooling the mixture to -20° C.
  2. additionwas added
  3. stirringThe mixture was stirred for 2 hours at 0° C.
  4. customThe mixture was evaporated to dryness under reduced pressure
  5. washThe organic solution was washed with water
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1550a2c42379468ab53a6c235e7abb7c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243043

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