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Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate → Racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid

HRID 1376841
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1376841
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([S:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:35]3[C:39]([O:41]C(C)(C)C)=[O:40])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([S:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 53798384Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Produkt 1

HCID 54438830Racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acidAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 200 mg of the product of Step B dissolved in 4 ml of 66% formic acid was stirred at 50° C. for 2 hours, after which the solution was cooled and filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was re-dissolved in ethanol. The solvent was evaporated and 20 ml of ether were added with stirring for 30 minutes. Then, the crude products was separated and chromatographed on silica and eluted with a mixture of methylene chloride and methanol (8-2). After crystallization from ether, 70 mg of racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid melting at >210° C. (decomposes) were obtained.

Aufarbeitung

  1. temperatureafter which the solution was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. dissolutionthe residue was re-dissolved in ethanol
  5. customThe solvent was evaporated
  6. addition20 ml of ether were added
  7. stirringwith stirring for 30 minutes
  8. customThen, the crude products was separated
  9. customchromatographed on silica
  10. washeluted with a mixture of methylene chloride and methanol (8-2)
  11. customAfter crystallization from ether

Quellen und Nachweise

ORD-Eintrag
ord-ae9747bf9d2f4c4c9a2c836262cf18d8
Quelldatensatz
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05663164

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