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

HRID 1087440Notes

Reaction equation

HRID 1087440 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[SH:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]2[N:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[C:22]2[N:21]=1.B(F)(F)F.O>C(#N)C>[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C@@H:9]1[S:14][CH2:15][C:6]([CH2:5][S:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]3[N:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[C:22]3[N:21]=1)=[C:7]2[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6356Boron trifluorideHCID 4413287-Aminocephalosporanic acidHCID 178429728HCID 178429728, compound

Product 1

HCID 18646195(6R,7R)-7-amino-3-[[(3-carboxy-7-methylpyrazolo-[1,5-a]pyri-midine-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of 4.00 g of (7R)-7-aminocephalosporanic acid and 3.34 g of 5-mercapto-7-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid in 20 ml of acetonitrile was treated with 25 ml of a 20 percent solution of boron trifluoride in acetonitrile and the mixture was stirred at 20° for 1.5 hours. 150 ml of cold water were added and the mixture was stirred at 0° for 1.5 hours. The precipitate was filtered off under suction and dried. There was obtained (6R,7R)-7-amino-3-[[(3-carboxy-7-methylpyrazolo[1,5-a]pyri-midine-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid as an almost colorless powder.

Workup

  1. stirringthe mixture was stirred at 0° for 1.5 hours
  2. filtrationThe precipitate was filtered off under suction
  3. customdried

Sources & evidence

ORD record
ord-a7cbe37d3c6d4394bf065979082083ae
Source dataset
uspto-grants-1991_07
Patent number
US05036064

Reaction notes

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