Ethyl Acetate → HCID 88767746, Verbindung

HRID 1707187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1707187
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([O:15][CH2:16][C:17]1[CH2:18][S:19][C@@H:20]2[CH:27]([NH2:28])[C:26](=[O:29])[N:21]2[C:22]=1[C:23]([OH:25])=[O:24])(=[O:14])[CH3:13].ClC(Cl)C([O:34][N:35]=[C:36]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:37](Cl)=[O:38])=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(#N)C.CC(N(C)C)=O.C(#N)C.CCO>[C:12]([O:15][CH2:16][C:17]1[CH2:18][S:19][C@@H:20]2[C@H:27]([NH:28][C:37](=[O:38])[C:36](=[N:35][OH:34])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:26](=[O:29])[N:21]2[C:22]=1[C:23]([OH:25])=[O:24])(=[O:14])[CH3:13]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 54057496HCID 54057496, VerbindungHCID 88783842HCID 88783842, Verbindung

Produkt 1

HCID 88767746HCID 88767746, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 21187609acetonitrile N,N-dimethylacetamideLösungsmittel

Versuchsvorschrift

To a suspension of 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid p-toluenesulphonic acid salt (4.8 g) in acetonitrile:dimethylacetamide (6:1, 25 ml.) was added dropwise with stirring at room temperature a 3 M solution of 2-dichloroacetoxyimino-2-phenylacetyl chloride (syn isomer) in acetonitrile (5 ml.). The reaction was stirred at room temperature until the solution was homogeneous, then poured into saturated aqueous sodium bicarbonate solution. The solution was washed with ethyl acetate, acidified to pH 1.0 (2 N-hydrochloric acid) and extracted with ethyl acetate. The combined extracts were washed with water, dried and concentrated to ca. 10 ml. The concentrate was added dropwise to petroleum spirit (b.p. 40°-60°) with vigorous stirring. This produced a gummy solid which was stirred with ethyl acetate (50 ml.) and the solution filtered and added dropwise to petroleum spirit (300 ml.). The precipitated solid was filtered and dried to give the title acid (1.47 g; 29%), [α]D +57° (c 0.7 DMSO) λmax. (EtOH) 253.5 nm (ε 15,800).

Aufarbeitung

  1. additionwas added dropwise
  2. washThe solution was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried
  6. concentrationconcentrated to ca. 10 ml
  7. additionThe concentrate was added dropwise to petroleum spirit (b.p. 40°-60°) with vigorous stirring
  8. customThis produced a gummy solid which
  9. filtrationthe solution filtered
  10. additionadded dropwise to petroleum spirit (300 ml.)
  11. filtrationThe precipitated solid was filtered
  12. customdried
  13. customto give the title acid (1.47 g; 29%), [α]D +57° (c 0.7 DMSO) λmax

Quellen und Nachweise

ORD-Eintrag
ord-144db97e463d4726a4e3a79e823756eb
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04209616

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