tert-Butanol → tert-Butyl 2-chloro-2-oxoacetate

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Reaction Steps

Oxalyl chloride (12.4 μL. 0.1 mmol) and t-butyl alcohol (13.1 μL) were combined in ether (0.3 mL) under nitrogen at 0° C. The resulting mixture was stirred for 30 minutes at room temperature. The solvent was evaporated under vacuum to form chloro-oxo-acetic acid t-butyl ester, which was then dissolved in DCM (0.7 mL) and combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methylpentanoic acid ethyl ester (33.4 mg, 98 μmol). Et3N (43.6 μL,) at 0° C. was added and the resulting mixture was stirred for 30 minutes at room temperature. The solvent were evaporated and the residue was dissolved in 1:1 TFA:DCM and stirred for 1 hour. AcOH was added and the product was purified by preparative HPLC to yield the title compound (7 mg, purity 95%). MS m/z [M+H]+ calc'd for C23H27NO6, 414.18; found 414.4.

Provenance & Evidence