7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid synthesis

Yield:-

Reaction Conditions:

with sodium hydroxide;thiourea in water;

Steps:

12.b EXAMPLE 12

b. A suspension of 2-carboxy-7-chloroacetamido-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (290.5 mg.) in water (8 cc.) is brought to pH 7 by adding normal sodium hydroxide solution (1 cc.). Thiourea (114 mg.) is added to the solution obtained and the whole is stirred at 30°C for 48 hours. The reaction mixture is then left at 4°C for 24 hours, the precipated solid is collected by filtration and dried to yield 7-amino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (150 mg.; 7-ADCA) as a white solid, the characteristics of which are as follows: Rf = 0.40 [silica gel; 0.5 M solution of sodium chloride]

References:

US3975385,1976,A