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

HRID 1755860Notes

Reaction equation

HRID 1755860 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:33])[NH:29][CH:30]=[N:31][CH:32]=2)[CH:23]=[CH:24][C:25]=1[OH:26].B(F)(F)F.CCOCC>S1(CCCC1)(=O)=O.ClCCl>[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:33][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]=[CH:30][N:29]=1)=[C:7]2[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 199178705-(3,4-dihydroxyphenyl)-4(3H)-pyrimidinethione

Product 1

HCID 54106762(6R,7R)-7-Amino-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 88.8%

Reagents, catalysts & solvents 1

HCID 69712587Dichloromethane sulpholaneSolvent

Procedure

7-Aminocephalosporanic acid (220 mg) (0.81 mmol) and 250 mg (1.04 mmol) of 5-(3,4-dihydroxyphenyl)-4(3H)-pyrimidinethione are suspended in 8 ml of sulpholane/dichloromethane (1:1 v/v) and treated with 5 ml of boron trifluoride diethyl etherate while stirring. After 18 hours the mixture is concentrated in a vacuum and the residue is washed with diethyl ether. Then, 2 ml of ethanol and 4 ml of water are added thereto and sodium hydrogen carbonate is added until pH 5 has been reached. The product is filtered off under suction, washed with water and diethyl ether and dried in a high vacuum at room temperature. There are obtained 311 mg of (6R,7R)-7-amino-3-[[[5-(3,4-dihydroxyphenyl)-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 18 hours the mixture is concentrated in a vacuum
  2. washthe residue is washed with diethyl ether
  3. additionThen, 2 ml of ethanol and 4 ml of water are added
  4. additionsodium hydrogen carbonate is added until pH 5
  5. filtrationThe product is filtered off under suction
  6. washwashed with water and diethyl ether
  7. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-47e26d90d4ac40329d5deeda02672a54
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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