Sodium Azide → HCID 118005624, compound

Temperature

70 °C

To a solution of 2-chloroethyl 4-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranoside (1.53 g, 4.57 mmol) in DMF (45 mL) at rt was added sodium azide (360 mg, 5.54 mmol). After stirring at 70° C. for 16 hr, the reaction mixture was cooled down to rt and poured onto ice water (200 mL) and extracted with CH2Cl2 (3×100 mL). The organic layers were combined and washed with brine (2×100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (120 g), eluting with 0-100% EtOAc in hexanes to give the title compound. TLC: silica gel, hexane/EtOAc: 1/1, Rf=0.55. 1H NMR (CDCl3) δ 7.37-7.28 (5 H, m), 4.84-4.71 (2H, m), 4.55-4.52 (1 H, m), 4.22-4.07 (1H, m), 4.03-3.98 (1H, m), 3.94-3.86 (2H, m), 3.79-3.71 (2H, m), 3.56-3.51 (1H, m), 3.48-3.36 (3H, m).

1. temperaturethe reaction mixture was cooled down to rt
2. additionpoured onto ice water (200 mL)
3. extractionextracted with CH2Cl2 (3×100 mL)
4. washwashed with brine (2×100 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography on silica gel (120 g)
9. washeluting with 0-100% EtOAc in hexanes

ORD record

ord-343842c0569046119da8749117f94ad8

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09427475B2