Imidazole → methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[(tert-butyldiphenylsilyl)oxy]propanoate

Participants

Reaction Steps

(R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid methyl ester (2.2 mg, 10 mmol) was dissolved in THF (20 ml). Imidazole (818 mg, 12 mmol) and TBDPS chloride (2.9 ml, 11 mmol) were added. The mixture was stirred at rt overnight. The mixture was then partitioned between CH2Cl2 and water (30 ml/30 ml). The organic layer was concentrated and the residue was purified by column chromatography (6/1, Hexanes/EtOAc) to give (R)-2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester (3.3 g, 72%).

Provenance & Evidence