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Acetone → 7beta-Amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid

HRID 992692
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 992692
[NH2:1][C@@H:2]1[C:32](=[O:33])[N:4]2[C:5]([C:16]([O:18]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:17])=[C:6]([S:9][CH2:10][C:11]3[CH:12]=[N:13][NH:14][CH:15]=3)[CH2:7][S:8][C@H:3]12.Cl.C(OCC)(=O)C.CC(C)=O>C(O)=O>[NH2:1][C@@H:2]1[C:32](=[O:33])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([S:9][CH2:10][C:11]3[CH:15]=[N:14][NH:13][CH:12]=3)[CH2:7][S:8][C@H:3]12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 70122266Diphenylmethyl 7beta-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

Produkt 1

HCID 701245417beta-Amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acidAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

Diphenylmethyl 7β-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (810 mg) was dissolved in formic acid (3.2 ml) below 5° C. and herein concentrated hydrochloric acid (0.71 ml) was added thereto at the same temperature. After the reaction mixture was stirred at the room temperature for an hour, it was poured into a mixture of ethyl acetate (50 ml) and acetone (25 ml), resulting precipitate was collected by filtration, and dried under reduced pressure. The precipitate was suspended in a mixture of water (6.0 ml) and acetone (2.5 ml). After the suspension was dissolved at pH 7.0 with saturated sodium bicarbonate solution, and adjusted to pH 4.5 with 1N-hydrochloric acid. The mixture was stirred at the room temperature for 30 minutes, and then resulting precipitate was collected, washed with acetone (5.0 ml), and dried under reduced pressure to give 7β-amino-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid (0.36 g) was obtained.

Aufarbeitung

  1. customresulting precipitate
  2. filtrationwas collected by filtration
  3. customdried under reduced pressure
  4. additionThe precipitate was suspended in a mixture of water (6.0 ml) and acetone (2.5 ml)
  5. dissolutionAfter the suspension was dissolved at pH 7.0 with saturated sodium bicarbonate solution
  6. stirringThe mixture was stirred at the room temperature for 30 minutes
  7. customresulting precipitate
  8. customwas collected
  9. washwashed with acetone (5.0 ml)
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-428c172c9bb348039702a97a76a9e606
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06468995B1

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