Ammonium Chloride → Methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate

Participants

Reaction Conditions

Reaction Steps

Ammonium chloride (1.04 g) and iron (777 mg) were added to a solution of Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate (Intermediate 2, step C, 2.15 g) in EtOH (21.5 ml), THF (8.6 ml), and Water (8.6 ml). The reaction mixture was refluxed at 80° C. for 3 hours. It was then cooled, filtered through celite and the solvent was removed under reduced pressure to get dark brown residue. The residue was taken in water and extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4 and concentrated to get dark brown residue which was purified by column on silica gel in 2.5:7.5 EtOAc:chloroform to get yellow sticky solid which was crystallized in DCM/pet ether to yield 1.82 g (91%) of the title compound. 1HNMR (DMSO-d6, 300 MHz): δ 8.59 (d, 1H), 8.15 (s, 1H), 7.42 (d, 2H), 6.63 (d, 2H), 5.76 (bs, 2H), 4.31 (m, 1H), 3.67 (s, 3H), 2.27 (m, 1H), 0.91 (d, 6H); MS (ES+): m/z 334 (M+1).

Provenance & Evidence