Boron trifluoride → HCID 22855043, compound

HRID 1755833Notes

Reaction equation

HRID 1755833 reaction equation
[SH:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][NH:12][S:13]([C:16]3[CH:36]=[CH:35][C:19]4[O:20]C(C5C=CC=CC=5)(C5C=CC=CC=5)[O:22][C:18]=4[CH:17]=3)(=[O:15])=[O:14])[N:10]=[C:6]2[N:5]=[C:4]([CH3:37])[CH:3]=1.CC(O[CH2:42][C:43]1[CH2:52][S:51][C@@H:46]2[C@H:47]([NH2:50])[C:48](=[O:49])[N:45]2[C:44]=1[C:53]([OH:55])=[O:54])=O.B(F)(F)F>C(#N)C>[NH2:50][C@@H:47]1[C:48](=[O:49])[N:45]2[C@@H:46]1[S:51][CH2:52][C:43]([CH2:42][S:1][C:2]1[N:7]3[N:8]=[C:9]([CH2:11][NH:12][S:13]([C:16]4[CH:36]=[CH:35][C:19]([OH:20])=[C:18]([OH:22])[CH:17]=4)(=[O:14])=[O:15])[N:10]=[C:6]3[N:5]=[C:4]([CH3:37])[CH:3]=1)=[C:44]2[C:53]([OH:55])=[O:54]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 4413287-Aminocephalosporanic acidHCID 178429717HCID 178429717, compound

Product 1

HCID 22855043HCID 22855043, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[[7-Mercapto-5-methyl-s-triazolo[1,5-a]pyrimidin-2-yl]methyl]-2,2-diphenyl-1,3-benzodioxol-5-sulphonamide (0.27 g) and 0.14 g of 7-aminocephalosporanic acid are stirred at room temperature for 4 hours with 3.0 ml of a 20% solution of boron trifluoride in acetonitrile. After the addition of 5 ml of ice-water the reaction mixture is partitioned between water and ethyl acetate. The pH value is adjusted to 7.0 with 3N aqueous sodium hydroxide solution. The phases are separated. The aqueous phase is adjusted to pH 2.0 with concentrated aqueous hydrochloric acid. The precipitate formed is filtered off. The still moist precipitate is dissolved in trifluoroacetic acid and stirred at room temperature for 2 hours. The trifluoroacetic acid is evaporated in a water-jet vacuum and the residue is treated with ethyl acetate. The precipitate is filtered off and dried under a high vacuum. There is obtained 0.2 g of (6R,7R)-7-amino-3-[[[2-[(3,4-dihydroxybenzenesulphonamido)methyl]-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a pale beige powder.

Workup

  1. customis partitioned between water and ethyl acetate
  2. customThe phases are separated
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. dissolutionThe still moist precipitate is dissolved in trifluoroacetic acid
  6. customThe trifluoroacetic acid is evaporated in a water-jet vacuum
  7. additionthe residue is treated with ethyl acetate
  8. filtrationThe precipitate is filtered off
  9. customdried under a high vacuum

Sources & evidence

ORD record
ord-90f3ea5fc6324782b67e2696fb7f6f7d
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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