Methanol → Methyl 3-azido-2-hydroxypropionate

To an ice-cold mixture of methyl 3-amino-2-hydroxypropionate hydrochloride (19) (27.1 g, 0.17 mol) in water (100 mL) and dichloromethane (100 mL) was added sodium carbonate (19.82 g, 0.187 mol) and CuSO4. 5H2O (0.3 g, 1.2 mmol) with stirring. Triflylazide from experiment 10(B)(i) (crude, 44.6 g, 0.25 mol) was added dropwise keeping the reaction temperature at 0-5° C. Methanol (about 100 mL) was added until the reaction mixture became homogeneous. The reaction mixture was allowed to come to room temperature and then stirred for 20 h. Water (500 mL) was added and the aqueous solution thoroughly extracted with dichloromethane (5×100 mL). The combined organic layers were washed with water (2×200 mL), saturated sodium carbonate (2×200 mL), and then dried (anhydrous sodium sulfate). After removal of the solvent, the residue was chromatographed over silica gel. Elution with 30% ethyl acetate in hexanes furnished the product as a colorless oil (14.0 g; Yield: 57%) Rf 0.57 (30% ethyl acetate in hexanes).

1. customat 0-5° C
2. customto come to room temperature
3. stirringstirred for 20 h
4. extractionthe aqueous solution thoroughly extracted with dichloromethane (5×100 mL)
5. washThe combined organic layers were washed with water (2×200 mL), saturated sodium carbonate (2×200 mL)
6. dry with materialdried (anhydrous sodium sulfate)
7. customAfter removal of the solvent
8. customthe residue was chromatographed over silica gel
9. washElution with 30% ethyl acetate in hexanes

ORD record

ord-7c25f9a433a94596837ca08a72d607fe

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399460B2