Hydrochloric Acid → Diphenylmethyl 7beta-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate

HRID 992680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992680
C([NH:3][C@@H:4]1[C:35](=[O:36])[N:6]2[C:7]([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:8]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH2:9][S:10][C@H:5]12)=O.Cl.C(OCC)(=O)C.[OH-].[Na+]>CO>[NH2:3][C@@H:4]1[C:35](=[O:36])[N:6]2[C:7]([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:8]([S:11][CH2:12][C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[CH2:9][S:10][C@H:5]12

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 88157711Diphenylmethyl 7beta-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate

Produkt 1

HCID 70124524Diphenylmethyl 7beta-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylateAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of diphenylmethyl 7β-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (13.70 g, 26.5 m mol) in methanol (65 ml) was added dropwise conc. HCl (11.0 ml) at room temperature and the mixture was stirred at the same temperature for 2.8 hours. The mixture was poured into a mixture of ethyl acetate and ice water and adjusted to pH 7 by addition of 5N NaOH aq. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with ethyl acetate to give diphenylmethyl 7β-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (5.16 g).

Aufarbeitung

  1. washwas washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-19382d95f85649178a32e4f082b30479
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06468995B1

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