Dichloromethane → (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-(hydroxymethyl)-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

HRID 1755904Notes

Reaction equation

HRID 1755904 reaction equation
[SH:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([NH:13][OH:14])=[O:12])[N:10]=[C:6]2[N:5]=[C:4]([CH2:15][OH:16])[CH:3]=1.CC(O[CH2:21][C:22]1[CH2:31][S:30][C@@H:25]2[C@H:26]([NH2:29])[C:27](=[O:28])[N:24]2[C:23]=1[C:32]([OH:34])=[O:33])=O.B(F)(F)F.CCOCC.ClCCl>S1(CCCC1)(=O)=O.ClCCl>[NH2:29][C@@H:26]1[C:27](=[O:28])[N:24]2[C@@H:25]1[S:30][CH2:31][C:22]([CH2:21][S:1][C:2]1[N:7]3[N:8]=[C:9]([C:11](=[O:12])[NH:13][OH:14])[N:10]=[C:6]3[N:5]=[C:4]([CH2:15][OH:16])[CH:3]=1)=[C:23]2[C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 178523964HCID 178523964, compound

Product 1

HCID 22855050(6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-(hydroxymethyl)-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 66.9%

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Conditions

Temperature
0 °C

Procedure

7-Mercapto-N-hydroxy-5-(hydroxymethyl)-s-triazolo[1,5-a]pyrimidine-2-carboxamide (300 mg) (1.24 mmol) and 305 mg (1.12 mmol) of 7-aminocephalosporanic acid are suspended in 50 ml of sulpholane/dichloromethane (1:1 v/v). 5 ml of boron trifluoride diethyl etherate are added thereto at 0° C. The reaction mixture is stirred at 0° C. for 21/2 hours and at room temperature for 24 hours. After the addition of 30 ml of dichloromethane the mixture is stirred for 15 minutes and subsequently filtered. The suction filter material is dissolved in water and adjusted to pH 5 with saturated aqueous sodium hydrogen carbonate solution. The precipitated product is filtered off under suction and washed in succession with water, dichloromethane and diethyl ether. There are obtained 340 mg of (6R,7R)-7-amino-3-[[[2-(hydroxycarbamoyl)-5-(hydroxymethyl)-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 beige powder.

Workup

  1. customat 0° C
  2. waitat room temperature for 24 hours
  3. stirringis stirred for 15 minutes
  4. filtrationsubsequently filtered
  5. filtrationThe suction filter material
  6. dissolutionis dissolved in water
  7. filtrationThe precipitated product is filtered off under suction
  8. washwashed in succession with water, dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-2584516e3fd94a03b22b961a7bc29f10
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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