Boron trifluoride → HCID 18646194, compound

HRID 846892Notes

Reaction equation

HRID 846892 reaction equation
[NH4+].[SH:2][C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]([NH-:14])=[O:13])=[C:7]2[N:6]=[C:5]([CH3:15])[CH:4]=1.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.[OH-].[Na+]>C(#N)C.O>[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:2][C:3]1[N:8]3[N:9]=[CH:10][C:11]([C:12](=[O:13])[NH2:14])=[C:7]3[N:6]=[C:5]([CH3:15])[CH:4]=1)=[C:22]2[C:31]([OH:33])=[O:32]

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 4413287-Aminocephalosporanic acidHCID 178429709HCID 178429709, compound

Product 1

HCID 18646194HCID 18646194, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.80 g of 7-mercapto-5-methylpyrazolo-[1,5-a]pyrimidine-3-carboxamide ammonium salt and 3.38 g of (7R)-7-aminocephalosporanic acid was treated with 25 ml of a 20 percent solution of boron trifluoride in acetonitrile and stirred at 20° for 40 minutes. The reaction mixture was treated with 30 ml of water and the pH was adjusted to 3.5 by means 28 percent aqueous sodium hydroxide solution. The precipitate thus formed was filtered off under suction and was chromatographed on OPTI-UP (C12) (ANTEC AG, CH-Bennwil) using water as the eluent. There was obtained (6R,7R)-7-amino-3-[[(3-carbamoyl-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. customThe precipitate thus formed
  2. filtrationwas filtered off under suction
  3. customwas chromatographed on OPTI-UP (C12) (ANTEC AG, CH-Bennwil)

Sources & evidence

ORD record
ord-327d26afc7fa44048243e02fc3aaa3f3
Source dataset
uspto-grants-1992_08
Patent number
US05138066

Reaction notes

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