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6-[acetoxy-(5-ethoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester → 6-(5-ethoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-ylmethylene)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

HRID 1744943
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1744943
[N+](C1C=CC(C[O:9][C:10]([C:12]2[N:13]3[CH:16]([S:17][CH:18]=2)[C:15]([CH:20](OC(=O)C)[C:21]2[N:32]=[C:31]4[N:23]([C:24]5[CH2:25][CH2:26][CH2:27][C:28]=5[C:29]([O:33][CH2:34][CH3:35])=[N:30]4)[CH:22]=2)(Br)[C:14]3=[O:40])=[O:11])=CC=1)([O-])=O.[H][H]>C1COCC1.P([O-])([O-])([O-])=O>[CH2:34]([O:33][C:29]1[C:28]2[CH2:27][CH2:26][CH2:25][C:24]=2[N:23]2[C:31](=[N:32][C:21]([CH:20]=[C:15]3[C:14](=[O:40])[N:13]4[CH:16]3[S:17][CH:18]=[C:12]4[C:10]([OH:11])=[O:9])=[CH:22]2)[N:30]=1)[CH3:35]
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Komponenten

5

Edukt 2

HCID 684429206-[acetoxy-(5-ethoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 684434556-(5-ethoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-ylmethylene)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1061
Phosphate
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-[acetoxy-(5-ethoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1.03 gram, 1.565 mmol) was suspended in 20 ml THF and 20 ml pH=6.5 aqueous phosphate buffer. The mixture was then subjected to 45 psi hydrogen for two hours. Then it was filtered through a pad of celite and concentrated in vacuo to remove most of the THF. The solution was then cooled to zero degree and basified to pH=8 with 1 N sodium hydroxide. Then it was purified via reverse phase HPLC using 1 liter of water followed by 5%˜25% acetonitrile and water. Water was then removed through concentrate in vacuo and 100 mg of product was collected.

Aufarbeitung

  1. filtrationThen it was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customto remove most of the THF
  4. temperatureThe solution was then cooled to zero degree and basified to pH=8 with 1 N sodium hydroxide
  5. customThen it was purified via reverse phase
  6. customWater was then removed
  7. concentrationthrough concentrate in vacuo and 100 mg of product
  8. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-6f712424cc084c318e8a1275a9489837
Quelldatensatz
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07018997B2

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