Phosphate → HCID 14230828, compound

HRID 615109Notes

Reaction equation

HRID 615109 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16](S(C(F)(F)F)(=O)=O)[CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCCC1C=NCCC2.P([O-])([O-])([O-])=O>C(Cl)Cl>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]=[C:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 14230826HCID 14230826, compound

Product 1

HCID 14230828HCID 14230828, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl 7-phenoxyacetamido-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (88 mg.) in methylene chloride (2 ml.) was added a solution of 1,5-diazabicyclo[5,4,0]undec-5-ene (24 mg.) in methylene chloride (0.5 ml.) at -20° C. After stirring at the same temperature for 45 minutes, the reaction mixture was poured into a chilled phosphate buffer solution (pH 7) and then extracted with ethyl acetate. The extract was washed with water and an aqueous solution of sodium chloride. Drying over magnesium sulfate and removal of the solvent left an oil (69 mg.), which was chromatographed on silica gel (2 g.) with a mixed solvent of benzene and ethyl acetate (5:1 by volume) to give an oil (33 mg.) of benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]oct-2-ene-2-carboxylate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil (69 mg.), which
  5. customwas chromatographed on silica gel (2 g.) with a mixed solvent of benzene and ethyl acetate (5:1 by volume)

Sources & evidence

ORD record
ord-59ce4281741c4bb2908c8d85f4eb5f44
Source dataset
uspto-grants-1985_02
Patent number
US04497738

Reaction notes

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