Methanol → HCID 57520946, compound

A solution of -(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyldibenzoate (100 mg, 0.2 mmol) in DCM (10 mL) was treated with DAST (137 mg, 0.8 mmol) for 30 min at −78° C. After stirring overnight at room temperature, the reaction was quenched with satd. aqueous NaHCO3 (10 mL), extracted with DCM (3×10 mL), washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to give the crude product as a white syrup (80 mg), which was dissolved into MeOH (5 mL) and treated with K2CO3 (10 mg, 0.07 mmol) for 3 h at room temperature. The reaction mixture was neutralized by AcOH and concentrated. The residue was purified by a silica gel column, eluted with 5%-10% MeOH in DCM to give -(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-(fluoromethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol as white solid (10 mg, 17%, two steps). (ES, m/z): [M+H]+ 263.0; 1H NMR (300 MHz, D2O) δ 6.30 (d, J=6.3 Hz, 1H), 4.49-4.69 (dd, J=57, 3.3 Hz, 1H), 4.11-4.15 (m, 1H), 3.93-4.01 (m, 5H), 3.70-3.82 (m, 1H), 3.59-3.69 (m, 1H), 2.24-2.34 (m, 2H).

1. customthe reaction was quenched with satd
2. extractionaqueous NaHCO3 (10 mL), extracted with DCM (3×10 mL)
3. washwashed with brine (10 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under vacuum
6. customto give the crude product as a white syrup (80 mg), which
7. concentrationconcentrated
8. customThe residue was purified by a silica gel column
9. washeluted with 5%-10% MeOH in DCM

ORD record

ord-1e5eb871b5cf440c8a5574cd103cb7d3

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09243020B2