1,1'-(Diazomethylene)bis(benzene) → Benzhydryl 7-amino-3-hydroxycepham-4-carboxylate

HRID 704258Notes

Reaction equation

HRID 704258 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][CH:17]1[C:28](=[O:29])[N:19]2[CH:20]([C:25]([OH:27])=[O:26])[CH:21]([OH:24])[CH2:22][S:23][C@H:18]12>C(OCC)(=O)C.CS(C)=O>[NH2:16][CH:17]1[C:28](=[O:29])[N:19]2[CH:20]([C:25]([O:27][CH:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:26])[CH:21]([OH:24])[CH2:22][S:23][C@H:18]12

Participants

5

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 13072520(6R)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid

Product 1

HCID 67948072Benzhydryl 7-amino-3-hydroxycepham-4-carboxylateYield 68.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of diphenyldiazomethane (1.7 mol) in ethyl acetate (2.13 l) was added to a mixture of 7-amino-3-hydroxycepham-4-carboxylic acid (186 g) in dimethyl sulfoxide (1.5 l). The mixture was stirred at room temperature for 32 hours and filtered. To the filtrate was added water and the mixture was extracted with ethyl acetate. The extract was washed three times with water, dried over magnesium sulfate and filtered, and the filtrate was evaporated in vacuo. The residue was tritulated with diisopropyl ether to give benzhydryl 7-amino-3-hydroxycepham-4-carboxylate (223 g) as powder.

Workup

  1. filtrationfiltered
  2. additionTo the filtrate was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed three times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-900b555376a0482588374ad06f8b734d
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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