5-Thiazoleacetic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]- synthesis

Yield:723278-39-5 76%

Reaction Conditions:

with sodium hydroxide;water in tetrahydrofuran;methanol at 20;

Steps:

1.n

Sodium hydroxide (234 ML of a 1.0 N solution in water) was added to a solution of methyl (2-((TERT-BUTOXYCARBONYL) AMINO)-1, 3-thiazol-5-yl) acetate (31.8 g, 117 mmol) in tetrahydrofuran (240ML) and methanol (240ML). The solution was stirred overnight at ambient temperature. The organic solvents were removed under reduced pressure. The residue was acidified with aqueous citric acid to pH 3.5. The product was extracted into ethyl acetate, dried over magnesium sulphate, filtered, concentrated under reduced pressure and triturated with diethyl ether to give (2-((TERT-BUTOXYCARBONYL) AMINO)-1, 3-thiazol-5-yl) acetic acid (23. 1G, 76 % yield) as a pale orange solid: 'H-NMR (DMSO d6): 7.10 (s, 1H), 3.70 (s, 2H), 1.40 (s, 9H): MS (-ve ESI): 257 (M-H)-

References:

WO2004/58752,2004,A1 Location in patent:Page 67