4-Aminobenzoic Acid → 4-(Methylsulfonamido)benzoic acid

Participants

Reaction Steps

4-Aminobenzoic acid is reacted with methanesulfonyl chloride (Compound 19) to give N-(4-carboxyphenyl)methanesulfonamide. 2-Triethylsilyl-4-furaldehyde (Compound 18) is reacted with N-(4-carboxyphenyl)methanesulfonamide and lithium diisopropylamide. The resulting 4-[1-hydroxy-2-N-(4-carboxyphenyl)sulfonamido]-ethyl-2-triethylsilylfuran is esterified with dodecanoyl chloride in the presence of triethylamine. Oxidizing this ester with singlet oxygen, under conditions as in Example 1, gives the title furanone.

Provenance & Evidence