1,1'-(Diazomethylene)bis(benzene) → HCID 131718250, compound

HRID 257814Notes

Reaction equation

HRID 257814 reaction equation
[NH2:1][C@@H:2]1[C:16](=[O:17])[N:4]2[C:5]([C:13]([OH:15])=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7][S:8][C@H:3]12.[C:18]1([C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N+]=[N-])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.CS(C)=O>[NH2:1][C@@H:2]1[C:16](=[O:17])[N:4]2[C:5]([C:13]([O:15][CH:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 12802218HCID 12802218, compound

Product 1

HCID 131718250HCID 131718250, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 7β-amino-3-azidomethyl-3-cephem-4-carboxylic acid (20.7 g, 81 mmol) in a mixture of dichloromethane (250 ml) and dimethyl sulfoxide (250 ml) was added dropwise a solution of diphenyldiazomethane (17.53 g, 90 mmol) in dichloromethane (150 ml). The mixture was stirred at room temperature for 68 h, filtered, the filtrate was concentrated under reduced pressure. The residual sticky mass was taken in ethyl acetate (250 ml) and washed successively with saturated sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulfate; solvent was removed under reduced pressure to give a residue which was purified over a silica column using dichloromethane-ethyl acetate (1:1) to give 18.4 g (54%) of a mixture of Δ2 and Δ3 -cephems. The mixture was directly used for the next step without further separation.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washwashed successively with saturated sodium bicarbonate solution, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customsolvent was removed under reduced pressure
  6. customto give a residue which
  7. customwas purified over a silica column

Sources & evidence

ORD record
ord-e5ae5026a2fe4edfbf1487beac25d585
Source dataset
uspto-grants-1993_11
Patent number
US05264430

Reaction notes

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