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

HRID 1109341Notes

Reaction equation

HRID 1109341 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([SH:11])[CH:3]=1.CC(O[CH2:16][C:17]1[CH2:26][S:25][C@@H:20]2[C@H:21]([NH2:24])[C:22](=[O:23])[N:19]2[C:18]=1[C:27]([OH:29])=[O:28])=O>B(F)(F)F.C(#N)C>[NH2:24][C@@H:21]1[C:22](=[O:23])[N:19]2[C@@H:20]1[S:25][CH2:26][C:17]([CH2:16][S:11][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=1)=[C:18]2[C:27]([OH:29])=[O:28]

Participants

5

Reactant 2

HCID 4413287-Aminocephalosporanic acidHCID 178429727HCID 178429727, compound

Product 1

HCID 67821284(6R,7R)-7-amino-3-[[(7-methylpyrazolo-[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6356Boron trifluorideSolvent

Procedure

0.70 g of 7-methylpyrazolo[1,5-a]pyrimidine-5-thiol and 1.15 g of (7R)-7-amino-cephalosporanic acid were dissolved in 10 ml of a 20 percent solution of boron trifluoride in acetonitrile and stirred at room temperature for 1 hour. The reaction mixture was concentrated and taken up in 10 ml of water. The solid was filtered off under suction. There was obtained (6R,7R)-7-amino-3-[[(7-methylpyrazolo[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a reddish powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe solid was filtered off under suction

Sources & evidence

ORD record
ord-38981e05fbb940778271a8d29be12a6f
Source dataset
uspto-grants-1994_06
Patent number
US05319140

Reaction notes

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