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An Efficient Synthesis Of Methyl 2-Methoxy-4-Amino-5-Chloro-Benzoate-(Carbonyl-14C)
January 29, 2010
•White Paper: An Efficient Synthesis Of Methyl 2-Methoxy-4-Amino-5-Chloro-Benzoate-(Carbonyl-14C)
By Analytical Bio-Chemistry Laboratories (ABC Labs)
Methyl 2-Methoxy-4-Amino-5-Chloro-Benzoate- [Carbonyl-14] (MMACB-14C) is an important intermediate in the synthesis of several Carbon-14 labeled API's. Compound 1 was needed as an intermediate for a synthesis that required seven additional steps that resulted in an overall yield of 36%. A better route was requred to make the synthesis more efficient.
Previous synthesis, of (MMACB-14C) has been performed using 4-amino-2-hydroxy-[carbonyl-14C] benzoic acid as the starting material. This labeled benzoic acid was produced from the commercially available 2-methoxy- 4-nitroaniline in 43% yield. It should be noted that the substitution with labeled K14CN, required the use of CuCN for the reaction to proceed.
The remainder of the synthesis proceeds with methylation followed by chlorination. This published method includes the conversion of the ester to the acid, which would be omitted. Removal of this step would presumably raise the overall yield to 20% and should not affect the chlorination.
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