Hydrochloric Acid → HCID 178472571, compound

Participants

Reaction Steps

A solution of 398 (3.75 g, 9.46 mmol), 24 (1.63 g, 11.4 mmol), EtOH (30 mL) and NaOEt (3.86 g, 11.4 mmol) was heated to 85° C. and stirred overnight. The reaction was cooled to RT and quenched reaction by addition of 4N HCl in dioxane (2.37 mL, 9.46 mmol) and the solution concentrated. The crude product was purified by reverse phase chromatography (Biotage 40 M C18 using a C18 samplet loaded using water) eluting with a MeCH/H2O chromatography (0-60% MeCN) over 30 column volumes to afford 1.25 g (37%) of (S)-ethyl-4-(4,6-dihydroxy-2-(tetrahydro-2H-pyran-4-ylamino) pyrimidin-5-yl)-2-hydroxybutanoate (400): MS m/z (APCI-pos) M+1=342.1.

Provenance & Evidence