Phosphate → HCID 68441815, compound

HRID 2216582Notes

Reaction equation

HRID 2216582 reaction equation
C(O[CH:5]([C:28]1[CH:37]=[C:31]2[C:32](=[O:36])[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]>[O:13]=[C:12]1[N:11]2[C@H:7]([S:8][CH:9]=[C:10]2[C:14]([OH:16])=[O:15])/[C:6]/1=[CH:5]\[C:28]1[CH:37]=[C:31]2[C:32](=[O:36])[O:33][CH2:34][CH2:35][N:30]2[N:29]=1

Participants

5

Reactant 2

HCID 1061PhosphateHCID 865914314-nitrobenzyl (5R)-6-[(acetyloxy)(4-oxo-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 68441815HCID 68441815, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitrobenzyl (5R)-6-[(acetyloxy)(4-oxo-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 (0.22 g, 0.37 mmol) in THF (15 ml), under nitrogen, was added 15 ml of a phosphate buffer solution (0.5M, pH 6.5), and 80 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 0.07 g of a yellow solid; MS m/e 320 (MH+); 1H NMR (DMSO-d6) δ 4.55–4.57 (m, 2H), 4.76–4.80 (m, 2H), 6.50 (s, 1H), 6.63 (s, 1H), 7.58 (s, 1H), 7.76 (s, 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

Sources & evidence

ORD record
ord-a44a82d039134b7ea77b603dab92a679
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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