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Phosphate → (5R,6Z)-6-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1158923
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158923
C(O[CH:5]([C:28]1[CH:36]=[C:31]2[CH2:32][O:33][CH2:34][CH2:35][N:30]2[N:29]=1)[C:6]1(Br)[C:12](=[O:13])[N:11]2[C@@H:7]1[S:8][CH:9]=[C:10]2[C:14]([O:16]CC1C=CC([N+]([O-])=O)=CC=1)=[O:15])(=O)C.P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[N:29]1[N:30]2[C:31]([CH2:32][O:33][CH2:34][CH2:35]2)=[CH:36][C:28]=1/[CH:5]=[C:6]1\[C@@H:7]2[N:11]([C:12]\1=[O:13])[C:10]([C:14]([OH:16])=[O:15])=[CH:9][S:8]2
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Komponenten

5

Edukt 2

HCID 1061PhosphateHCID 118472844-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Produkt 1

HCID 11847461(5R,6Z)-6-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.35 g, 0.6 mmol) in THF (20 ml), under nitrogen, was added 20 ml of a phosphate buffer solution (0.5M, pH 6.5), and 120 mg of 10% Pd/C. The mixture was hydrogenated at 40-50 psi for 3 hr, and then filtered through Celite. The filter pad was washed with THF, and the filtrate was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and evaporated. The residue was washed with ether to give 0.09 g of a yellow solid; HRMS: calcd for C13H11N3O4S, 305.0470; found (ESI+), 306.05434; 1H NMR (DMSO-d6) δ 4.07-4.09 (t, 2H), 4.13-4.17 (t, 2H), 4.82 (s, 2H), 6.36 (s, 1H), 6.55 (s, 1H), 7.17 (s, 1H), 7.55 (s, 1H), 12.80 (bs, 1H).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. washThe filter pad was washed with THF
  3. extractionthe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customevaporated
  7. washThe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-0e3cffb7efd7423a9170572b68ec7f98
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07812014B2

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