Dichloromethane → (6R,7R)-7-amino-3-[[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-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 1755915Notes

Reaction equation

HRID 1755915 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([SH:11])[N:8]2[N:12]=[C:13]([CH2:15][OH:16])[N:14]=[C: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>S1(CCCC1)(=O)=O.ClCCl>[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:11][C:9]1[N:8]3[N:12]=[C:13]([CH2:15][OH:16])[N:14]=[C:7]3[N:6]=[C:5]([C:3](=[O:4])[NH:2][OH:1])[CH:10]=1)=[C:23]2[C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178523962HCID 178523962, compound

Product 1

HCID 22855054(6R,7R)-7-amino-3-[[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-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 40.4%

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Hydroxy-2-(hydroxymethyl)-7-mercapto-s-triazolo[1,5-a]pyrimidine-5-carboxamide (190 mg) (0.79 mmol) and 193 mg (0.71 mmol) of 7-amino-cephalosporanic acid are suspended in 20 ml of sulpholane/dichloromethane (1:1 v/v). 4.2 ml of boron trifluoride diethyl etherate are added thereto at 0° C. The mixture is stirred at 0° C. for 2 hours and at room temperature for 20 hours. 80 ml of dichloromethane are added. The precipitated material is separated and dissolved in water. The mixture is adjusted to pH 4 by the addition of saturated aqueous sodium hydrogen carbonate solution. The precipitated product is filtered off under suction and washed in sequence with water, ethanol and diethyl ether. There are obtained 130 mg of (6R,7R)-7-amino-3-[[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-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. customat 0° C
  2. customThe precipitated material is separated
  3. dissolutiondissolved in water
  4. additionThe mixture is adjusted to pH 4 by the addition of saturated aqueous sodium hydrogen carbonate solution
  5. filtrationThe precipitated product is filtered off under suction
  6. washwashed in sequence with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-c7950d0bef4d466883eb5224485c2d2e
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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