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

HRID 2351128Notes

Reaction equation

HRID 2351128 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 dipheyldiazomethane (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-fcbab095cbda4a9e93d93d5004d3e20c
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

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