Hydrochloric Acid → HCID 21426449, Verbindung

HRID 258705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258705
C(O[CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:26])[CH:10]2[NH:14][C:15](=[O:25])[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[S:22]([CH3:24])=[O:23])[C:7]=1[C:27]([OH:29])=[O:28])(=O)C.C(=O)(O)[O-].[Na+].[CH3:35][C:36]1[S:37][C:38](=[S:41])[NH:39][N:40]=1.Cl>O>[C:27]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][S:41][C:38]1[S:37][C:36]([CH3:35])=[N:40][N:39]=1)[CH:10]([NH:14][C:15](=[O:25])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22]([CH3:24])=[O:23])[C:9]2=[O:26])([OH:29])=[O:28]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 21426442HCID 21426442, Verbindung

Produkt 1

HCID 21426449HCID 21426449, VerbindungAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-Acetoxymethyl-2-carboxy-7-[(2-methylsulphinylimidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]-oct-2-ene (8.5 g.) and sodium bicarbonate (1.62 g.) are dissolved in water (75 cc.). A solution of 2-methyl-5-thioxo-1,3,4-thiadiazoline (2.54 g.) and sodium bicarbonate (1.62 g.) in water (75 cc.) is added and the mixture is heated at 60° C. for 6 hours. After cooling, the pH is adjusted to 6 by adding hydrochloric acid (4 N) and the mixture is washed twice with ethyl acetate (a total of 200 cc.). The mixture is acidified to pH 2 by adding hydrochloric acid (4 N); a product precipitates and is filtered off and dried under reduced pressure (1 mm.Hg) to give 7.9 g. of product. Recrystallisation from methanol (25 cc.), filtration and drying under reduced pressure (0.1 mm.Hg) gives 2-carboxy-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-7-[(2-methylsulphinyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (2.7 g.), m.p. 227° C. (with decomposition), [α]D20 = -35° ± 1° (c= 1, dimethylformamide).

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe mixture is washed twice with ethyl acetate (a total of 200 cc
  3. additionby adding hydrochloric acid (4 N)
  4. customa product precipitates
  5. filtrationis filtered off
  6. customdried under reduced pressure (1 mm.Hg)
  7. customto give 7.9 g
  8. customRecrystallisation
  9. filtrationfrom methanol (25 cc.), filtration
  10. customdrying under reduced pressure (0.1 mm.Hg)

Quellen und Nachweise

ORD-Eintrag
ord-a4e1b44022af4feaa72a302e5bdb4dc0
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04034088

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