Boron trifluoride etherate → (6R,7R)-7-Amino-3-[[[5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755851Notes

Reaction equation

HRID 1755851 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.[OH:19][C:20]1[CH:21]=[C:22]([C:27]2[C:28](=[S:39])[NH:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:31][CH:32]=2)[CH:23]=[CH:24][C:25]=1[OH:26].B(F)(F)F.CCOCC>ClCCl.S1(CCCC1)(=O)=O>[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:39][C:28]1[C:27]([C:22]3[CH:23]=[CH:24][C:25]([OH:26])=[C:20]([OH:19])[CH:21]=3)=[CH:32][N:31]=[C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:29]=1)=[C:7]2[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 199179865-(3,4-dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinethione

Product 1

HCID 54291490(6R,7R)-7-Amino-3-[[[5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Procedure

7-Aminocephalosporanic acid (162 mg) (0.6 mmol) and 216 mg (0.66 mmol) of 5-(3,4-dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinethione are suspended in 7 ml of dichloromethane/sulpholane (1:1 v/v). 4 ml of boron trifluoride diethyl etherate are added thereto while stirring. After 16 hours the mixture is concentrated in a high vacuum at room temperature, the residue is washed with diethyl ether and dissolved in about 3 ml of water. Sodium hydrogen carbonate is added thereto until the pH is adjusted to 5. Then, 1 ml of diethyl ether and 0.5 ml of ethanol are added thereto. The precipitated product is filtered off under suction, washed in succession with water, ethanol and ether and dried in a high vacuum at room temperature. There are obtained 250 mg of (6R,7R)-7-amino-3-[[[5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Workup

  1. concentrationAfter 16 hours the mixture is concentrated in a high vacuum at room temperature
  2. washthe residue is washed with diethyl ether
  3. dissolutiondissolved in about 3 ml of water
  4. additionSodium hydrogen carbonate is added
  5. additionThen, 1 ml of diethyl ether and 0.5 ml of ethanol are added
  6. filtrationThe precipitated product is filtered off under suction
  7. washwashed in succession with water, ethanol and ether
  8. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-8d5b0f2f44f04906a0b6ca9ee8355027
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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