Water → HCID 53909123, compound

HRID 1461065Notes

Reaction equation

HRID 1461065 reaction equation
[SH:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]2[N:12]=[CH:13][C:14]([C:15]([NH2:17])=[O:16])=[C:4]2[N:3]=1.CC(O[CH2:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34])=O.B(F)(F)F.O>C(#N)C>[NH2:30][C@@H:27]1[C:28](=[O:29])[N:25]2[C@@H:26]1[S:31][CH2:32][C:23]([CH2:22][S:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[N:5]3[N:12]=[CH:13][C:14]([C:15](=[O:16])[NH2:17])=[C:4]3[N:3]=1)=[C:24]2[C:33]([OH:35])=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6356Boron trifluorideHCID 4413287-Aminocephalosporanic acidHCID 178513769HCID 178513769, compound

Product 1

HCID 53909123HCID 53909123, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 1.60 g of 5-mercapto-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide and 1.66 g of (7R)-7-aminocephalosporanic acid in 120 ml of acetonitrile was treated while stirring with 20 ml of a 20 percent solution of boron trifluoride in acetonitrile and stirred at 20° for a further 5 hours. 100 ml of water were added and the mixture was concentrated in a vacuum to a volume of about 80 ml. The pH was adjusted to 2.8 with 25 percent aqueous ammonia. After stirring for 1 hour, the precipitate obtained was filtered, washed in succession with water, acetone and ether and dried. There was obtained (6R,7R)-7-amino-3-[[(3-carbamoyl-7-(trifluoromethyl)pyrazolo[1,5-a]-pyrimidin-5-yl)thio]methyl]-8-oxo-5thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. additionwas treated
  2. concentrationthe mixture was concentrated in a vacuum to a volume of about 80 ml
  3. stirringAfter stirring for 1 hour
  4. customthe precipitate obtained
  5. filtrationwas filtered
  6. washwashed in succession with water, acetone and ether
  7. customdried

Sources & evidence

ORD record
ord-58ffd95e222c4f8fa5224ccaefcc11c7
Source dataset
uspto-grants-1991_12
Patent number
US05073550

Reaction notes

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