Ethyl bromoacetate → 3-[2-Azido-2-(2-ethoxycarbonylmethoxyethoxy)ethoxy]benzoic acid

To a solution of 3-[2-azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid (0.535 g, 2 mmol) in dry THF (6 ml) was added NaH (60% dispersion, 0.246 g, 6 mmol) at 0° C. After 10 minutes, ethyl 2-bromoacetate (0.488 ml, 4.4 mmol) was added. The reaction was then warmed up to room temperature and stirred for 4 hours. The reaction was quenched by pouring it into ice-cold water (50 ml). The mixture was extracted with DCM (2×50 ml) and the-DCM extracts were discarded. The aqueous layer was then acidified to pH 2 with 1 N HCl, and extracted with DCM (2×50 ml). These DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography (1×20 cm). The title compound, eluted with 2% methanol in DCM, was obtained as an oil (0.223 g, 31.6%). ES-MS, m/z 351.95 (M−1).

1. customThe reaction was quenched
2. additionby pouring it into ice-cold water (50 ml)
3. extractionThe mixture was extracted with DCM (2×50 ml)
4. extractionextracted with DCM (2×50 ml)
5. dry with materialdried over MgSO4
6. customevaporated under reduced pressure
7. customThe residue was purified by column chromatography (1×20 cm)
8. washThe title compound, eluted with 2% methanol in DCM

ORD record

ord-1fa7139b42d44eae8f263e46d1bd5ac5

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178360B2