Methyl bromoacetate → HCID 57839105, compound

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).

1. customis quenched by the addition of 1 M KH2PO4
2. additiondiluted with ethyl acetate
3. customThe phases are separated
4. washthe organic phase is washed with 1 M KH2PO4 and saturated aqueous NaHCO3
5. extractionThe combined aqueous phases are back-extracted with ethyl acetate
6. dry with materialThe combined organic phases are dried over Na2SO4
7. filtrationThe mixture is filtered
8. concentrationconcentrated
9. customto give an oil which
10. customis purified by flash chromatography on a BIOTAGE 40S column
11. washeluting with 500 mL heptane

ORD record

ord-702c03c52a77401ea3a8b0c4cee02070

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589094B2