Ammonia → 7beta-amino-3-[(1-formamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid

HRID 483017

Reaktionsgleichung

Reaktionsgleichung von HRID 483017
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[CH:19]([NH:21][N:22]1[C:26]([SH:27])=[N:25][N:24]=[N:23]1)=[O:20].CS(O)(=O)=O.N>C(#N)C.O>[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:27][C:26]3[N:22]([NH:21][CH:19]=[O:20])[N:23]=[N:24][N:25]=3)[CH2:15][S:14][C@H:9]12

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 6395Methanesulfonic AcidHCID 4413287-Aminocephalosporanic acidHCID 1785239441-formamido-5-mercapto-1H-tetrazole

Produkt 1

HCID 704535727beta-amino-3-[(1-formamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acidAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2.45 g of 7β-aminocephalosporanic acid and 1.31 g of 1-formamido-5-mercapto-1H-tetrazole were dissolved in 13 ml of acetonitrile, and 4.32 g of methanesulfonic acid were added dropwise thereto at room temperature under stirring. The mixture was stirred at room temperature for 30 minutes and then at 50° C. for 4 hours. 15 ml of water were added to the reaction mixture, and said mixture was adjusted to pH 5 with 28% ammonia. The resultant precipitates were collected by filtration, washed with water and acetone, and then dried. 2.43 g of 7β-amino-3-[(1-formamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid were obtained as pale yellow powder.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. customThe resultant precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water and acetone
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-63383ba4e7ed4b9692a06fbaa23b2adc
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04576938

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