Potassium Carbonate → HCID 69082892, compound

Participants

Reaction Steps

A solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(azetidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (360 mg, 0.93 mmol) in methanol (5 mL) was treated with potassium carbonate (13 mg, 0.09 mmol) overnight at 40° C. The reaction mixture was concentrated under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, X-Bridge C18, 19*50 mm 3.5 um; mobile phase, Water with 0.05% NH4OH and CH3CN (3% CH3CN up to 9% in 5 min; Detector, UV 220 nm)] to give compound 3 as a white solid (100 mg, 40%). (ES, m/z) [M+H]+ 261.0; 1H NMR (300 MHz, DMSO+D2O) δ 6.25-6.27 (d, J=6.3 Hz, 1H), 3.92-3.96 (t, J=5.7 Hz, 1H), 3.83-3.88 (m, 4H), 3.68-3.71 (t, J=4.8 Hz, 1H), 3.55-3.58 (m, 1H), 3.25-3.42 (m, 3H), 2.21-2.26 (m, 2H).

Provenance & Evidence