Boron trifluoride etherate → HCID 136002475, compound

HRID 1755889Notes

Reaction equation

HRID 1755889 reaction equation
[SH:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:12]=[C:13]([OH:18])[C:14](=[CH:16][CH:17]=3)[OH:15])[N:10]=[C:6]2[N:5]=[C:4]([CH3:19])[CH:3]=1.CC(O[CH2:24][C:25]1[CH2:34][S:33][C@@H:28]2[C@H:29]([NH2:32])[C:30](=[O:31])[N:27]2[C:26]=1[C:35]([OH:37])=[O:36])=O.S1(CCCC1)(=O)=O.B(F)(F)F.CCOCC>ClCCl>[NH2:32][C@@H:29]1[C:30](=[O:31])[N:27]2[C@@H:28]1[S:33][CH2:34][C:25]([CH2:24][S:1][C:2]1[N:7]3[N:8]=[C:9]([C:11]4[CH:17]=[CH:16][C:14]([OH:15])=[C:13]([OH:18])[CH:12]=4)[N:10]=[C:6]3[N:5]=[C:4]([CH3:19])[CH:3]=1)=[C:26]2[C:35]([OH:37])=[O:36]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 31347SulfolaneHCID 4413287-Aminocephalosporanic acidHCID 178429706HCID 178429706, compound

Product 1

HCID 136002475HCID 136002475, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(7-Mercapto-5-methyl-s-triazolo[1,5-a]pyrimidin-2-yl)pyrocatechol (1.8 g) and 1.63 g of 7-amino-cephalosporanic acid are suspended in 30 ml of a 1:1 mixture of dichloromethane and sulpholane. 2.63 g of boron trifluoride etherate are added thereto at 3° C. and the solution is left at the same temperature for 11/2 hours. Thereafter, it is diluted dropwise with 60 ml of dichloromethane, the resulting precipitate is filtered off under suction, rinsed with diethyl ether and dissolved immediately in 40 ml of water. Sufficient 20% aqueous sodium hydroxide solution is added while cooling with ice until pH 3.1 has been reached, whereby the product precipitates. This is filtered off under suction, washed with a small amount of water and finally with 20 ml of acetone and dried in a vacuum at 0.1 mmHg. There are obtained 2.17 g of (6R,7R)-7-amino-3-[[[2-(3,4-dihydroxyphenyl)-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.

Workup

  1. filtrationthe resulting precipitate is filtered off under suction
  2. washrinsed with diethyl ether
  3. dissolutiondissolved immediately in 40 ml of water
  4. additionSufficient 20% aqueous sodium hydroxide solution is added
  5. temperaturewhile cooling with ice until pH 3.1
  6. customwhereby the product precipitates
  7. filtrationThis is filtered off under suction
  8. washwashed with a small amount of water and finally with 20 ml of acetone
  9. customdried in a vacuum at 0.1 mmHg

Sources & evidence

ORD record
ord-fda10cae58de4e5caeba1fca846c3ba9
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

Loading…