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

HRID 1607308Notes

Reaction equation

HRID 1607308 reaction equation
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.Cl.[NH2:35][C:36]1[S:40][N:39]=[C:38](/[C:41](=[N:45]/[O:46][CH3:47])/[C:42](Cl)=[O:43])[N:37]=1.P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl>[NH2:35][C:36]1[S:40][N:39]=[C:38](/[C:41](=[N:45]/[O:46][CH3:47])/[C:42]([NH:1][C@@H:2]2[C:20](=[O:21])[N:4]3[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]23)=[O:43])[N:37]=1

Participants

6

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 11708267BistrimethylsilylacetamidHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 19930550(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl chloride;hydrochloride

Product 1

HCID 88417261(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 240 ml of dichloromethane is suspended 9.06 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid. To the suspension is added 28.9 g of bistrimethylsilylacetamide and the mixture is stirred at room temperature until complete dissolution and cooled in an ice-water bath. To this solution, 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetyl chloride hydrochloride prepared from 5.83 g of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoximinoacetic acid and 6.02 g of phosphorus pentachloride in 90 ml of dichloromethane is added and the mixture is stirred for a while. 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 11.8 (82% yield) g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-00caf91569d24211b844453e050eaf9d
Source dataset
uspto-grants-1989_09
Patent number
US04864022

Reaction notes

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