Citric Acid → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acid

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Reaction Steps

A 100 mL round bottom flask was charged with 2-(S)-tert-butoxycarbonylamino-3-thiazol-2-yl-propionic acid benzyl ester (370 mg, 1.02 mmol), tetrahydrofuran (9.0 mL), water (0.9 mL), and lithium hydroxide (48 mg, 1.14 mmol) and the resulting mixture was stirred at room temperature for 6 h. The resulting mixture was then neutralized with 10% citric acid and extracted with ethyl acetate (100 mL), and dichlormethane (100 mL). The organic layers were dried with MgSO4, filtered, and concentrated in vacuo to yield (S)-2-(tert-butoxycarbonylamino)-3-(thiazol-2-yl)propanoic acid. MS (ES+) 273 (M+1).

Provenance & Evidence