Hydrochloric Acid → (5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 7-formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylate

HRID 34268

Reaktionsgleichung

Reaktionsgleichung von HRID 34268
[CH:1]([NH:3][CH:4]1[C:21](=[O:22])[N:6]2[C:7]([C:18]([OH:20])=[O:19])=[C:8]([CH2:11][S:12][N:13]3[CH2:17][S:16][N:15]=[CH:14]3)[CH2:9][S:10][C@H:5]12)=[O:2].[CH2:23]1OC1C.Br[C:28]1[O:29][C:30](=[O:35])[O:31][C:32]=1[CH2:33]C.Cl>CN(C=O)C.CCOC(C)=O>[CH:1]([NH:3][CH:4]1[C:21](=[O:22])[N:6]2[C:7]([C:18]([O:20][CH2:23][C:28]3[O:29][C:30](=[O:35])[O:31][C:32]=3[CH3:33])=[O:19])=[C:8]([CH2:11][S:12][N:13]3[CH2:17][S:16][N:15]=[CH:14]3)[CH2:9][S:10][C@H:5]12)=[O:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6378Propylene OxideHCID 704066334-Bromo-methyl-5-methyl-1,3-dioxolene-2-oneHCID 886407317-Formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylic acid

Produkt 1

HCID 131715666(5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 7-formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A suspension of 7-formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylic acid (1.07 g, 3 mmole), KHCO3 (1.0 g, 10 mmole) and propylene oxide (1 ml) in DMF (5 ml) was cooled to 5° C. and treated with 4-bromo-methyl-5-methyl-1,3-dioxolene-2-one (0.87 g, 4.5 mmole). After stirring at 5° C. for 5 hr, the reaction mixture was poured into a mixture of aq HCl (pH 3) (70 ml) and EtOAc (250 ml). The EtOAc layer was separated and washed successively with aq HCl (pH 3) (70 ml×2), 10% K2HPO4 buffer (pH 7) (70 ml×2) and saturated aq NaCl (50 ml). The EtOAc solution was dried (MgSO4) and concentrated in vacuo. The residue was triturated with ether (300 ml) and the resulting precipitate was filtered to give the title compound ( 0.45 g).

Aufarbeitung

  1. customThe EtOAc layer was separated
  2. washwashed successively with aq HCl (pH 3) (70 ml×2), 10% K2HPO4 buffer (pH 7) (70 ml×2) and saturated aq NaCl (50 ml)
  3. dry with materialThe EtOAc solution was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether (300 ml)
  6. filtrationthe resulting precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-be25827142204a54ba9cfb56b41c74fe
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761409

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