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Hydrochloric Acid → HCID 70636145, Verbindung

HRID 596843
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596843
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C:14]([CH:17]=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8].O1CC[CH2:39][CH2:38]1.C([Mg]Br)C.Cl>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:20])[C:14]([CH:17]([OH:18])[CH2:38][CH3:39])=[CH:15][S:16][C@H:11]12)=[O:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 88777142HCID 88777142, VerbindungHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 70636145HCID 70636145, VerbindungAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857
Ethyl Acetate
Lösungsmittel

Reaktionsbedingungen

Temperatur
-73 °C

Versuchsvorschrift

To a cooled (-73° C.), stirred solution of 1.559 g. of benzhydryl 7-(2-thienylacetamido)-3-formyl-2-cephem-4-carboxylate and 20 ml. of dry tetrahydrofuran was added 3.13 ml. of 2.88 M. ethyl magnesium bromide. After the reaction mixture was allowed to stir for four minutes at -73° C., 10 ml. of 1N.HCl was added and the solution allowed to warm to 0° C. The reaction mixture was transferred to a separatory funnel with the aid of cold ethyl acetate and cold 1N.HCl. The organic layer was separated and washed twice with cold 1N.HCl and twice with brine and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided a product residue which was chromatographed on silica gel using a toluene-ethyl acetate gradient to give 0.140 g. of the starting 3-formyl-2-cephem ester and 0.507 g. (30.6 percent) of the title product as a mixture of diasteromers:

Aufarbeitung

  1. stirringto stir for four minutes at -73° C.
  2. temperatureto warm to 0° C
  3. customThe organic layer was separated
  4. washwashed twice with cold 1N
  5. dry with materialHCl and twice with brine and then dried over anhydrous sodium sulfate
  6. customEvaporation in vacuo to dryness
  7. customprovided a product residue which
  8. customwas chromatographed on silica gel using a toluene-ethyl acetate gradient
  9. customto give 0.140 g

Quellen und Nachweise

ORD-Eintrag
ord-e4f5ddd6e0e34fef81046c8671477ac0
Quelldatensatz
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04012380

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