Ammonium Chloride → (R)-ethyl-3-azido-2-hydroxypropionate

Temperature

75 °C

Ethyl-(2R)-2,3-epoxyproprionate (0.5 g, 4.3 mmol), ammonium chloride (0.253 g, 4.73 mmol), and sodium azide (0.336 g, 5.17 mmol) were combined in DMF (8 mL), and the mixture was heated at 75° C. for 14 hours. The reaction was cooled to room temperature, and was partitioned between water and ether/hexanes (1:1 v/v). The phases were separated, and the organic phase was washed once each with water, brine, dried over MgSO4, filtered, and concentrated to an oil, which was purified by flash chromatography (silica gel/hexanes: 10% ethyl acetate) to give (R)-ethyl-3-azido-2-hydroxypropionate as a clear oil (0.47 g, 2.97 mmol, 69% yield). Rf 0.27 (hexanes: 10% EtOAc, v/v, p-anisaldehyde); MS m/e [M+Na]+ calcd 182.1, found 182.0.

1. temperatureThe reaction was cooled to room temperature
2. customwas partitioned between water and ether/hexanes (1:1 v/v)
3. customThe phases were separated
4. washthe organic phase was washed once each with water, brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated to an oil, which
8. customwas purified by flash chromatography (silica gel/hexanes: 10% ethyl acetate)

ORD record

ord-29c1d7a18f4c408eaee3527cd4f6be5f

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383596B2