Reaction #5257

Reaction equation

boron trifluoride

7-amino-cephalosporanic acid

benzyl alcohol

ammonium hydroxide

boron trifluoride

→

3-benzyloxy-7-amino-ceph-3-eme-4-carboxylic acid

Solvents

acetic acid

triethylamine

triethylamine

hydrochloric acid

hydrochloric acid

Conditions

Workup

1. 1
   Otherwere reacted
2. 2
   Otherto obtain 27.1 g of raw product
3. 3
   Otherprecipitation
4. 4
   Filtrationfiltered
5. 5
   Washthe product was rinsed with acetic acid, acetone
6. 6
   Otherether to obtain 4.6 of product
7. 7
   Filtrationvacuum filtered
8. 8
   WashThe product was rinsed with water, acetone

Procedure

Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 128 ml of the etherate of boron trifluoride, 126 ml of benzyl alcohol and 90 ml of triethylamine were reacted to obtain 27.1 g of raw product. 25 g of the said product and 250 ml of acetic acid were added to 25 ml of the etherate of boron trifluoride followed by the addition of 25 ml of triethylamine which caused precipitation. The mixture was vacuum filtered and the product was rinsed with acetic acid, acetone and then ether to obtain 4.6 of product. 4.8 g of the said product were dissolved at 45° C. in 20 ml of 2N hydrochloric acid and 8 ml of concentrated hydrochloric acid and the solution was treated with activated carbon. 6 ml of ammonium hydroxide were added to the mixture which was then vacuum filtered. The product was rinsed with water, acetone and then ether to obtain 2 g of 3-benzyloxy-7-amino-ceph-3-eme-4-carboxylic acid.

Source