Chlorotrimethylsilane → 7-(Di-2-thienylacetyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid

HRID 66644

Reaktionsgleichung

Reaktionsgleichung von HRID 66644
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[C@H:10]([NH:13][C:14]([CH2:16][C:17]3[S:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:24]([O-:26])=[O:25])=[O:3].[Na+].C[Si](C)(C)Cl.[SiH3]NC(=O)C(F)(F)F.[S:41]1[CH:45]=[CH:44][CH:43]=[C:42]1CC(Cl)=O>C(Cl)(Cl)Cl>[S:21]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:16]([C:42]1[S:41][CH:45]=[CH:44][CH:43]=1)[C:14]([NH:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:24]([OH:26])=[O:25])=[C:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[CH2:23][S:22][C@H:9]12)=[O:15]

Komponenten

6

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 1623622-Thiopheneacetyl chlorideHCID 23675321Cephalothin SodiumHCID 123231972Monosilyltrifluoroacetamide

Produkt 1

HCID 705412177-(Di-2-thienylacetyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A suspension of sodium cephalothin (1.18 g.) in anhydrous alcohol-free chloroform (10 ml.) is silylated by the addition of trimethylchlorosilane (1.1 ml.). After stirring for 30 minutes, monosilyltrifluoroacetamide (2.5 ml.) and 2-thienylacetyl chloride (2.0 ml.) are added to the suspension which is then heated to 45° C. The mixture is allowed to remain at this temperature for two days and then evaporated in vacuo to a residue which is dissolved in ethyl acetate (50 ml.) and washed three times with water. The ethyl acetate layer is dried over magnesium sulfate, filtered and the filtrate evaporated in vacuo to obtained a residue. The residue is dissolved in chloroform and precipitated with hexane three times, each time discarding the supernatent liquid. The 7-(di-2-thienylacetyl)amino-3-acetoxymethyl-3-cephem-4-carboxylic acid is obtained in a solvent-free form by freeze-drying from a solution in benzene.

Aufarbeitung

  1. waitto remain at this temperature for two days
  2. customevaporated in vacuo to a residue which
  3. dissolutionis dissolved in ethyl acetate (50 ml.)
  4. washwashed three times with water
  5. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customto obtained a residue
  9. customprecipitated with hexane three times

Quellen und Nachweise

ORD-Eintrag
ord-5bd39d5c12d448c8a6d7ff4fbd656c60
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342757

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