Methyl bromoacetate → HCID 57839105, compound

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Reaction Steps

Oxopiperazine v(0.4 g, 2.6 mmol) is combined with diisopropylethylamine (0.55 mL, 3.2 mmol) in 5 mL of methanol over ice, under N2. Methyl bromoacetate (0.27 mL, 2.9 mmol) is added dropwise and the solution is allowed to stir at ambient temperature for 2 hours, at which time it is quenched by the addition of 1 M KH2PO4 and diluted with ethyl acetate. The phases are separated and the organic phase is washed with 1 M KH2PO4 and saturated aqueous NaHCO3. The combined aqueous phases are back-extracted with ethyl acetate. The combined organic phases are dried over Na2SO4. The mixture is filtered and concentrated to give an oil which is purified by flash chromatography on a BIOTAGE 40S column eluting with 500 mL heptane followed by 1/1: heptane/EtOAc and 9/1:CH2Cl2/MeOH to afford v as colorless oil (0.29 g, 1.3 mmol, 50%). (MS: M+H:229.2).

Provenance & Evidence