tert-Butyl mercaptan → [3-(2-tert-Butylsulfanylmethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester

Participants

Reaction Steps

[3-(2-tert-Butylsulfanylmethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester was prepared according to the procedure described in Example 21, Step 8, using [3-(2-bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester and 2-methyl-2-propanethiol, which was reduced to [3-(4-amino-2-tert-butylsulfanylmethyl-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester as described in Example 21, Step 9. The amine was treated with pivaloyl chloride as described in Example 21, Step 10 to provide {3-[2-tert-butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-5-chloro-phenyl}-acetic acid methyl ester. Hydrolysis of the ester to the acid was carried out as outlined in Example 21, Step 11.

Provenance & Evidence