Methanol → HCID 89622329, compound

Participants

Reaction Steps

A suspension of Example 125 (88 mg, 194 μmol) in dichloromethane (5 ml) was treated with thionyl chloride (29 μl, 389 μmol), and the mixture was stirred at rt for 65 min. Another portion of thionyl chloride (29 μl, 389 μmol) was added, and stirring was continued for 1.5 h. An excess of methanol was then added, followed by dropwise addition of a 5.4 M solution of sodium methylate in methanol (84 mg, 1.56 mmol) until pH 8 was reached. After stirring for 3 days, the volatiles were evaporated under reduced pressure, and the residue was separated by preparative RP-HPLC (Reprosil C18, gradient 20-40% acetonitrile/0.2% aq. trifluoroacetic acid). The product fractions were evaporated to yield 19 mg of the title compound (21% of th.).

Provenance & Evidence