Acetic Acid → HCID 22475621, compound

Participants

Reaction Steps

The product from step 1 (500 mg, 1.9 mmol) and ethyl acetoacetate (0.27 mL, 2.1 mmol) were combined and dissolved in methanol (10 mL) at ambient temperature. To this solution was added glacial acetic acid (0.13 mL, 2.1 mmol) followed by sodium cyanoborohydride (194 mg, 3.1 mmol). After stirring 18 h, the solution was concentrated in vacuo and the resultant oil dissolved in ethyl acetate. The organics were washed with brine, dried over MgSO4, and concentrated. Purification by reverse phase HPLC using a gradient elution of 60:40 H2O/TFA:CH3CN to 0:100 H2O/TFA:CH3CN at 254 nm afforded the title compound as a white solid (440 mg, 61%): mp=103° C.

Provenance & Evidence