ethyl 2-(2-hydroxypropylamino)-2-oxoacetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 2-(2-hydroxypropylamino)-2-oxoacetate (2.1 g, 13 mmol) in DCM (30 mL) was added Dess-Martin periodinane (6.2 g, 14.6 mmol) in portions at 0° C. and the resulting mixture was stirred at room temperature for 16 h. The reaction was diluted with DCM and extracted with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried and concentrated to give crude product, which was purified via silica gel chromatography eluting with DCM/methanol (60:1) to give ethyl 2-oxo-2-(2-oxopropylamino)acetate (1.7 g, 81.2% yield) as yellow syrup. LCMS retention time 0.392 min, LCMS MH+ 174. extracted with saturated aqueous sodium bicarbonate solution and brine The organic layer was dried concentrated to give crude product, which was purified via silica gel chromatography eluting with DCM/methanol (60:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-aminopropan-2-ol (2 g, 26.6 mmol) and TEA (4.03 g, 39.9 mmol) in DCM (50 mL) was added ethyl 2-chloro-2-oxoacetate (4.36 g, 31.95 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 16 h. The mixture was diluted with DCM and extracted with brine. The organic layer was dried and concentrated to give a crude product which was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate (2:1) to give ethyl 2-(2-hydroxypropylamino)-2-oxoacetate (2.19 g, 51% yield) as yellow syrup. LCMS retention time 0.348 min, LCMS MH+ 176. extracted with brine The organic layer was dried concentrated to give a crude product which was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate (2:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate (10.7 g, 61.07 mmol) in DCM (100.0 mL), is added Dess Martin periodinane (25.9 g, 61.07 mmol) at 0° C. The reaction mixture is stirred at room temperature for 2 hours, diluted with water (100 mL) at 0° C., and extracted with DCM (2×100 mL). The combined organic layer is washed with water (2×50 mL) and saturated brine (50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude material is purified by silica gel chromatography, eluting with hexane:ethyl acetate (1:1) to give the title compound as a light yellow oil (9.2 g, 87.03%). ESI/MS m/z 174.1 (M+H)+. extracted with DCM (2×100 mL) The combined organic layer is washed with water (2×50 mL) and saturated brine (50 mL) dried over Na2SO4 evaporated under reduced pressure The crude material is purified by silica gel chromatography eluting with hexane:ethyl acetate (1:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1-amino-propan-2-ol (15.0 g, 199.7 mmol) in DCM (150.0 mL), is added triethylamine (43.30 mL, 299.56 mmol) at 0° C. Chloro-oxo-acetic acid ethyl ester (22.35 mL, 199.7 mmol) is added dropwise to the reaction mixture at 0° C. and the reaction mixture is stirred for 16 hours at room temperature. The mixture is diluted with water (100 mL) at 0° C., extracted with DCM (2×100 mL), washed with water (2×50 mL) and brine (50 mL), dried over Na2SO4, and evaporated to dryness. The crude product is purified by silica gel chromatography, eluting with hexane:ethyl acetate (3.0:7.0) to give the title compound as a pale yellow gel (10.7 g, 31.0%). ESI/MS m/z 176.2 (M+H)+. extracted with DCM (2×100 mL) washed with water (2×50 mL) and brine (50 mL) dried over Na2SO4 evaporated to dryness The crude product is purified by silica gel chromatography eluting with hexane:ethyl acetate (3.0:7.0)