Boron trifluoride → HCID 14852649, compound

HRID 1461075Notes

Reaction equation

HRID 1461075 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([SH:8])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N: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:8][C:6]1[N:5]3[N:9]=[CH:10][CH:11]=[C:4]3[N:3]=[C:2]([CH3:1])[CH:7]=1)=[C:18]2[C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 4413287-Aminocephalosporanic acidHCID 178429708HCID 178429708, compound

Product 1

HCID 14852649HCID 14852649, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.1 g of 5-methylpyrazolo[1,5-a]pyrimidine-7-thiol and 1.80 g of (7R)-7-aminocephalosporanic acid were stirred for 1 hour in 18 ml of a 20 percent solution of boron trifluoride in acetonitrile. The reaction mixture was concentrated, the residue was taken up in 15 ml of water, and the pH was adjusted to 2.5 with 2N sodium hydroxide solution. The precipitated product was filtered off under suction and dried. There was obtained (6R,7R)-7-amino-3-[[(5-methylpyrazolo[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. concentrationThe reaction mixture was concentrated
  2. filtrationThe precipitated product was filtered off under suction
  3. customdried

Sources & evidence

ORD record
ord-fa26bd6c54fe4eba8892056d340ead39
Source dataset
uspto-grants-1991_12
Patent number
US05073550

Reaction notes

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