Sodium Bicarbonate → HCID 21356563, compound

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Reaction Steps

5-Benzyloxycarbonylamino-2-(5-methyl-imidazol-1-yl)fluorobenzene (3.2 g, 9.85 mmol) was dissolved in dry tetrahydrofuran (40 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 6.81 ml). After stirring for 20 minutes at −70°, (R)-glycidylbutyrate (1.57 g, 10.09 mmol) was added at −70°. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated MeOH (10 ml), stirred 15 minutes, then poured into aqueous sodium bicarbonate (5%, 100 ml) and extracted with EtOAc (3×40 ml). The combined extracts were washed with brine (20 ml), dried (magnesium sulfate) and evaporated. and the residue purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 5 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated, to give the desired product (0.86 g). MS (ESP): 292 (MH+) for C14H14FN3O3.

Provenance & Evidence