Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

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Reaction Steps

To a solution of ethyl 2-[(tert-butoxycarbonyl)amino]thiazole-4-carboxylate (27.3 g, 100 mmol) prepared by the method of Kim and Kahn (Synlett, 1999, 8, 1239-1240) in 500 mL of THF at 0 C was added a solution of Red-A1 in toluene (80 mL of 65 wt % solution) dropwise. The reaction mixture was stirred for 1 d and then quenched with water and 1N HCl. Extracted 2×EtOAc and the EtOAc extracts were dried over MgSO4. The solution was filtered, concentrated by rotary evaporator, and chromatographed on SiO2 using 33% hexanes in EtOAC to give 20.5 g (89%) of 2-[(tert-butoxycarbonyl)amino]-4-hydroxymethylthiazole 42a. 1H-NMR (400 MHz, CDCl3): δ 6.98 (s, 1H), 4.81 (s, 2H), 1.81 (s, 9H).

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