Potassium Phosphate, Dibasic → HCID 10658069, compound

HRID 726986Notes

Reaction equation

HRID 726986 reaction equation
COC1C=C(C=CC=1OC)C[N:7]1[C:13](=[O:14])[C@@H:12]2[C@H:8]1[CH2:9][CH2:10][N:11]2[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].P([O-])([O-])(O)=O.[K+].[K+].[K]>C(#N)C.O>[O:14]=[C:13]1[C@@H:12]2[C@@H:8]([CH2:9][CH2:10][N:11]2[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[NH:7]1

Participants

6

Reactant 3

HCID 24450Potassium Phosphate, Dibasic2×HCID 5462222PotassiumHCID 86751735HCID 86751735, compound

Product 1

HCID 10658069HCID 10658069, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
100 °C

Procedure

135 g (0.34 mol) of benzyl (1S,5R)-6-(3,4-dimethoxy- benzyl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate were placed in 1.5 liters of acetonitrile. Thereto there was added a solution of 77 g (0.44 mol) of dipotassium hydrogen phosphate and 128 g (0.47 mol) of potassium peroxodisulphate in 660 ml of water and the mixture was heated to 100° C. The reaction time amounted to 2.5 hours. During this time the pH value of the mixture becomes acidic. This pH was held at about 5 by the portionwise addition of further dipotasium hydrogen phosphate. After completion of the reaction the acetonitrile was removed on a rotary evaporator and the aqueous residue was extracted with 3×250 ml of methylene chloride. The combined organic phases were washed once each time with 500 ml of 3% sodium hydrogen carbonate solution and 750 ml of saturated, aqueous sodium chloride solution and subsequently dried over magnesium sulphate. After concentration there was obtained a brown oil which was purified by chromatography [silica gel, 0.063-0.2 mm particle size, elution with 1) ethyl acetate:hexane =2:1; 2) ethyl acetate].

Workup

  1. customwas removed on a rotary evaporator
  2. extractionthe aqueous residue was extracted with 3×250 ml of methylene chloride
  3. washThe combined organic phases were washed once each time with 500 ml of 3% sodium hydrogen carbonate solution and 750 ml of saturated, aqueous sodium chloride solution
  4. dry with materialsubsequently dried over magnesium sulphate
  5. concentrationAfter concentration
  6. customthere was obtained a brown oil which
  7. customwas purified by chromatography [
  8. washsilica gel, 0.063-0.2 mm particle size, elution with 1) ethyl acetate

Sources & evidence

ORD record
ord-deea636b28c34abda661ff977c277df2
Source dataset
uspto-grants-1998_01
Patent number
US05712268

Reaction notes

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