Chloroform → 8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1076953Notes

Reaction equation

HRID 1076953 reaction equation
CC(OC[C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10](N)[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.C(Cl)(Cl)Cl>C(N(CC)CC)C>[O:12]=[C:11]1[N:8]2[CH:9]([S:14][CH2:15][CH:6]=[C:7]2[C:16]([OH:18])=[O:17])[CH2:10]1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 190919938-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

By treating 4 g. of the product of Example 1 (c) with 4.5 g. of 7-aminocephalosporanic acid which has been dissolved in 100 ml. of anhydrous chloroform with 6 ml. of triethylamine according to the procedure of Example 1 (d), 2.8 g. of 3-[(acetyloxy)methyl]-7β-[[(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)phenyl-acetyl[amino[-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is obtained which decomposes between 95° and 100°.

Workup

  1. additionBy treating 4 g

Sources & evidence

ORD record
ord-6ef50c0536a847a6bfccc48c9debd95c
Source dataset
uspto-grants-1976_05
Patent number
US03959259

Reaction notes

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