Dichloromethane → (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1607302Notes

Reaction equation

HRID 1607302 reaction equation
ClCCl.[NH2:4][C@@H:5]1[C:23](=[O:24])[N:7]2[C:8]([C:20]([OH:22])=[O:21])=[C:9]([CH2:12][O:13][C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])[CH2:10][S:11][C@H:6]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[NH2:37][C:38]1[S:42][N:41]=[C:40](/[C:43](=[N:47]/[O:48][CH2:49][CH3:50])/[C:44](Cl)=[O:45])[N:39]=1>CC(N(C)C)=O>[NH2:37][C:38]1[S:42][N:41]=[C:40](/[C:43](=[N:47]/[O:48][CH2:49][CH3:50])/[C:44]([NH:4][C@@H:5]2[C:23](=[O:24])[N:7]3[C:8]([C:20]([OH:22])=[O:21])=[C:9]([CH2:12][O:13][C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])[CH2:10][S:11][C@H:6]23)=[O:45])[N:39]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10825966(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl chlorideHCID 11708267BistrimethylsilylacetamidHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 15575218(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 69.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In 200 ml off dichloromethane is suspended 11 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid. To the suspension is added 14 g of bistrimethylsilylacetamide and the mixture is stirred at room temperature until complete dissolution and cooled in an ice-water bath. To this solution, 14 g of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetyl chloride is added and the mixture is stirred for a while, to which 6 g of dimethylacetamide is added. The whole mixture is stirred with ice-cooling for 60 minutes. The dichloromethane is evaporated off and the residue is dissolved in methyl ethyl ketone. The solution is washed with water and dried. The solvent is then evaporated off and diethyl ether is added to the residue to give a fine precipitate, which is collected by filtration, giving 12.5 g of the above-identified compound.

Workup

  1. temperaturecooled in an ice-water bath
  2. additionis added
  3. stirringThe whole mixture is stirred with ice-
  4. temperaturecooling for 60 minutes
  5. customThe dichloromethane is evaporated off
  6. dissolutionthe residue is dissolved in methyl ethyl ketone
  7. washThe solution is washed with water
  8. customdried
  9. customThe solvent is then evaporated off
  10. additiondiethyl ether is added to the residue
  11. customto give a fine precipitate, which
  12. filtrationis collected by filtration

Sources & evidence

ORD record
ord-fc22c53f84364a2f818aa72d29d96375
Source dataset
uspto-grants-1989_09
Patent number
US04864022

Reaction notes

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