Dichloromethane → (6R,7R)-7-amino-3-[[[2-(N-hydroxy-N-methylcarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,01oct-2-ene-2-carboxylic acid

HRID 1755898Notes

Reaction equation

HRID 1755898 reaction equation
[OH:1][N:2]([CH3:16])[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[CH2:21][C:22]1[CH2:31][S:30][C@@H:25]2[C@H:26]([NH2:29])[C:27](=[O:28])[N:24]2[C:23]=1[C:32]([OH:34])=[O:33])=O.B(F)(F)F.CCOCC.ClCCl>ClCCl.S1(CCCC1)(=O)=O>[NH2:29][C@@H:26]1[C:27](=[O:28])[N:24]2[C@@H:25]1[S:30][CH2:31][C:22]([CH2:21][S:13][C:12]1[N:7]3[N:6]=[C:5]([C:3](=[O:4])[N:2]([OH:1])[CH3:16])[N:15]=[C:8]3[N:9]=[C:10]([CH3:14])[CH:11]=1)=[C:23]2[C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178429719HCID 178429719, compound

Product 1

HCID 131719072(6R,7R)-7-amino-3-[[[2-(N-hydroxy-N-methylcarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,01oct-2-ene-2-carboxylic acidYield 73.1%

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Conditions

Temperature
10 °C

Procedure

N-Hydroxy-7-mercapto-N,5-dimethyl-s-triazolo[1,5-a]pyrimidine-2-carboxamide (53 mg) (0.22 mmol) and 54 mg (0.2 mmol) of 7-aminocephalosporanic acid are suspended in 1 ml of dichloromethane/sulpholane (1:1 v/v). 0.5 ml of boron trifluoride diethyl etherate is added thereto at 10° C. while stirring and the mixture is stirred at room temperature for a further 20 hours. Subsequently, about 10 ml of dichloromethane are added thereto, the insoluble material is filtered off under suction, dissolved in water and the product is precipitated by the addition of sodium hydrogen carbonate (pH→4). The precipitate is filtered off under suction and washed with water and ethanol. There are obtained 66 mg of (6R,7R)-7-amino-3-[[[2-(N-hydroxy-N-methylcarbamoyl)-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,01oct-2-ene-2-carboxylic acid as a white powder.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 20 hours
  2. filtrationthe insoluble material is filtered off under suction
  3. dissolutiondissolved in water
  4. customthe product is precipitated by the addition of sodium hydrogen carbonate (pH→4)
  5. filtrationThe precipitate is filtered off under suction
  6. washwashed with water and ethanol

Sources & evidence

ORD record
ord-410857398ba34f2ea6d0c92cd77a6dc1
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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