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 2216627Notes

Reaction equation

HRID 2216627 reaction equation
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

Participants

5

Reactant 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

Product 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 acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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
  8. customto give

Sources & evidence

ORD record
ord-d24c3731c0244bd8834caeb4b4188e69
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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