Boc-Ser(tBu)-OH → HCID 86722029, compound

Participants

Reaction Steps

Prepared according to the experimental procedure described in Preparation 61a from 1.07 g (3.39 mmol) of 1-amino-3-bromo-N-(3,5-difluorophenyl)-1H-pyrrole-2-carboxamide and 1.65 g (3.73 mmol) of (S)-3-tert-butoxy-2-(tert-butoxycarbonylamino)propanoic acid. After stirring the reaction mixture overnight, an excess of an additional 1.65 g (3.73 mmol) of the acid was added and the reaction stirred for yet 24 hours more. After precipitation and filtration of the product, two purification steps were needed. First by flash chromatography (70% to 100% DCM/hexanes) and a second purification by reverse phase chromatography (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%). 494 mg (26% yield) of the title compound were isolated as a white solid.

Provenance & Evidence