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 1654652Notes

Reaction equation

HRID 1654652 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 6344DichloromethaneSolvent

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-3yl)-2(Z)-methoximinoacetic acid and 6.02 g of phosphorus pentachloride in 90 ml of dischloromelthane 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 melthyl 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 precipiate, 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 melthyl 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 precipiate, which
  13. filtrationis collected by filtration

Sources & evidence

ORD record
ord-7fddbf9dbaf04bd1bf58895c005d1c81
Source dataset
uspto-grants-1995_04
Patent number
US05409919

Reaction notes

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