Imidazole → (2s)-2-Tert-butoxycarbonylamino-3-[5-(tert-butyl-dimethyl-silanyloxy)-1h-indol-3-yl]-propionic acid methyl ester

Participants

Reaction Steps

To a solution of Example 400A (1.20 g, 3.59 mmol) in DMF (20 mL) was added t-butyldimethylsilyl chloride (649 mg, 4.3 mmol), imidazole (293 mg, 4.3 mmol) and DMAP (50 mg) at rt. The reaction mixture was stirred at rt for 16 hours. EtOAc (100 mL) was added and the mixture was washed with brine (100 mL) and water (100 mL). The organic phase was concentrated and the residual oil was purified by flash chromatography (10-40% EtOAc in hexane) to give the desire product (1.6 g, 100%). MS (DCI) m/z 466 (M+18)+.

Provenance & Evidence