Reaction #5254

ord-dcaa90fa626041689c210e2969f0e25b

Reaction equation

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-amino-cephalosporanic acid
FB(F)F
boron trifluoride
C=CCO
allyl alcohol
→
C=CCOCC1=C(C(=O)O)N2C(=O)C(N)[C@H]2SC1
3-allyloxymethyl-7-amino-ceph-3-eme-4-carboxylic acid

Reactants

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-amino-cephalosporanic acid
FB(F)F
boron trifluoride
C=CCO
allyl alcohol

Reagents

None

Solvents

CCN(CC)CC
triethylamine

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwere reacted
  2. 2
    Otherthe 9 g of raw product was purified successively twice with hot hydrochloric acid and ammonium hydroxide

Procedure

Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of boron trifluoride, 136 ml of allyl alcohol and 115 ml of triethylamine were reacted and the 9 g of raw product was purified successively twice with hot hydrochloric acid and ammonium hydroxide to obtain 4.72 g of 3-allyloxymethyl-7-amino-ceph-3-eme-4-carboxylic acid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05243043uspto-grants-1993_09