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Hydrochloric Acid → HCID 21426469, Verbindung

HRID 258776
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 258776
[Na].C(O[CH2:6][C:7]1[CH2:14][S:13][CH:12]2[N:9]([C:10](=[O:25])[CH:11]2[NH:15][C:16](=[O:24])[CH2:17][C:18]2[S:19][C:20](=[O:23])[S:21][CH:22]=2)[C:8]=1[C:26]([OH:28])=[O:27])(=O)C.[S-]C#N.[K+].C(=O)(O)[O-].[Na+].[CH3:38][N:39]1[N:43]=[N:42][C:41](=[S:44])[NH:40]1.Cl.C(OC(C)C)(C)C>O.O1CCCC1>[C:26]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:7]=1[CH2:6][S:44][C:41]1[N:42]=[N:43][N:39]([CH3:38])[N:40]=1)[CH:11]([NH:15][C:16](=[O:24])[CH2:17][C:18]1[S:19][C:20](=[O:23])[S:21][CH:22]=1)[C:10]2=[O:25])([OH:28])=[O:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 199940532-methyl-2H-1,2,3,4-tetrazole-5-thiolHCID 21426457HCID 21426457, Verbindung

Produkt 1

HCID 21426469HCID 21426469, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The sodium salt of 3-acetoxymethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (6.1 g.) is dissolved in water (20 cc.). Potassium thiocyanate (26.6 g.), sodium bicarbonate (1.38 g.) and 2-methyl-5-thioxo-1,2,3,4-tetrazoline (1.9 g.) are added to this solution and the mixture is heated to 60° C. for 5 hours. After cooling, the reaction mixture is diluted with water (100 cc.), acidified to pH 5.8 by adding 4 N hydrochloric acid and washed with ethyl acetate (50 cc.). The aqueous phase is acidified to pH 1.6 by adding 4 N hydrochloric acid in the presence of ethyl acetate (200 cc.). After decanting the organic phase, the aqueous phase is extracted twice with ethyl acetate (a total of 200 cc.). The organic extracts are combined, washed twice with an 0.1 N hydrochloric acid solution (a total of 140 cc.) and then twice with water (a total of 200 cc.), dried over sodium sulphate, treated with decolourising charcoal, filtered and then concentrated to dryness under reduced pressure (20 mm Hg). The residue obtained is dissolved in tetrahydrofuran (25 cc.) and this solution is then added dropwise to isopropyl ether (300 cc.). A product precipitates which is isolated by filtration and dried under reduced pressure (0.1 mm Hg). 2-Carboxy-3[(2-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (5.1 g.) is thus obtained.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with ethyl acetate (50 cc.)
  3. additionby adding 4 N hydrochloric acid in the presence of ethyl acetate (200 cc.)
  4. customAfter decanting the organic phase
  5. extractionthe aqueous phase is extracted twice with ethyl acetate (a total of 200 cc
  6. washwashed twice with an 0.1 N hydrochloric acid solution (a total of 140 cc
  7. dry with material), dried over sodium sulphate
  8. additiontreated with decolourising charcoal
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg)
  11. customThe residue obtained
  12. customA product precipitates which
  13. customis isolated by filtration
  14. customdried under reduced pressure (0.1 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-0bc18ffa12024765b7834d77e0483534
Quelldatensatz
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04034090

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