Water → Water TFA acetonitrile

Participants

Reaction Steps

To a 7-mL scintillation vial containing Compound 10 (2.0 mg, 0.0032 mmol) was added sequentially tetrahydrofuran (200 μL), water (132 μL), sodium periodate (3.3 mg, 0.015 mmol), and a mixture consisting of potassium osmium tetroxide dihydrate (68 μg, 0.00018 mmol) and water (68 μL). The reaction mixture was stirred overnight in the dark at room temperature. HPLC (Gemini C18, 110 {acute over (Å)}, 5μ, 250×4.6 mm, 1 mL/min, 5/95/0.05→50/50/0.05 ACN/H2O/TFA) showed complete disappearance of starting material. The reaction mixture was placed in the freezer overnight and the desired product isolated the following day by prep HPLC (Gemini C18, 110 {acute over (Å)}, 10μ, 250×21.2 mm, 20 mL/min, 5/95/0.05→50/50/0.05 ACN/H2O/TFA)—split peak collected at about 20.5 min. The relevant fractions were combined and concentrated to afford the title intermediate (1 mg, 50% yield) as a clear solid; LC/MS ESI+ m/z 624, ESI− m/z 622.

Provenance & Evidence