Dichloromethane → (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755865Notes

Reaction equation

HRID 1755865 reaction equation
[OH:1][NH:2][C:3]([C:5]1[N:15]=[C:8]2[N:9]=[C:10]([CH3:14])[CH:11]=[C:12]([SH:13])[N:7]2[N:6]=1)=[O:4].CC(O[CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O.B(F)(F)F.CCOCC.ClCCl>S1(CCCC1)(=O)=O.ClCCl>[NH2:28][C@@H:25]1[C:26](=[O:27])[N:23]2[C@@H:24]1[S:29][CH2:30][C:21]([CH2:20][S:13][C:12]1[N:7]3[N:6]=[C:5]([C:3](=[O:4])[NH:2][OH:1])[N:15]=[C:8]3[N:9]=[C:10]([CH3:14])[CH:11]=1)=[C:22]2[C:31]([OH:33])=[O:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178429721HCID 178429721, compound

Product 1

HCID 22855051(6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Hydroxy-7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide and 3.4 g (12.5 mmol) of 7-aminocephalosporanic acid (3.1 g) (13.9 mmol) are suspended in 75 ml of sulpholane/dichloromethane (1:1 v/v). 7.5 ml of boron trifluoride etherate are added dropwise thereto at 0° C. and the mixture is stirred at 0° C. for 2.5 hours and at room temperature for 15 hours. 200 ml of dichloromethane are now added. After stirring for 30 minutes the mixture is suction filtered. The filter material is dissolved in 100 ml of water. The product is precipitated with saturated sodium hydrogen carbonate solution (pH~5), filtered off and washed with water, ethanol and ether. There are obtained 3.5 g of (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Workup

  1. stirringAfter stirring for 30 minutes the mixture
  2. filtrationfiltered
  3. dissolutionThe filter material is dissolved in 100 ml of water
  4. customThe product is precipitated with saturated sodium hydrogen carbonate solution (pH~5)
  5. filtrationfiltered off
  6. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-b3576f4a2abd4f508fb1e720816d09dc
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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