Dichloromethane → (6R,7R)-7-amino-3-[[[5-(hydroxycarbamoyl)-2-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 1755909Notes

Reaction equation

HRID 1755909 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([SH:11])[N:8]2[N:12]=[C:13]([CH3:15])[N:14]=[C: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:11][C:9]1[N:8]3[N:12]=[C:13]([CH3:15])[N:14]=[C:7]3[N:6]=[C:5]([C:3](=[O:4])[NH:2][OH:1])[CH:10]=1)=[C:22]2[C:31]([OH:33])=[O:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178432397HCID 178432397, compound

Product 1

HCID 22855055(6R,7R)-7-amino-3-[[[5-(hydroxycarbamoyl)-2-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 acidYield 67.4%

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Procedure

N-Hydroxy-7-mercapto-2-methyl-s-triazolo[1,5-a]pyrimidine-5-carboxamide (250 mg) (1.1 mmol) and 275 mg (1.0 mmol) of 7-amino-cephalosporanic acid are suspended in 15 ml of sulpholane/dichloromethane (1:1 v/v) and treated at 0° C. with 3.5 ml of boron trifluoride diethyl etherate. The mixture is stirred at 0°-5° C. for 2 hours and at room temperature for 3 hours. Subsequently, 60 ml of dichloromethane are added thereto. Insoluble material is filtered off under suction, dissolved in water and treated with saturated sodium bicarbonate solution until the pH value 3 has been reached. The precipitated product is filtered off under suction and washed in succession with water and diethyl ether. There are obtained 295 mg of (6R,7R)-7-amino-3-[[[5-(hydroxycarbamoyl)-2-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. filtrationInsoluble material is filtered off under suction
  2. dissolutiondissolved in water
  3. additiontreated with saturated sodium bicarbonate solution until the pH value 3
  4. filtrationThe precipitated product is filtered off under suction
  5. washwashed in succession with water and diethyl ether

Sources & evidence

ORD record
ord-e896fa81f385494883d21b2550446f9d
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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