Methanol → HCID 178446009, compound

Participants

Reaction Steps

To a suspension of (S,S)-2-[(acetylthio) methyl]-3,3,3-trifluoro-N-[3-methyl-1-(1H -tetrazol-5-yl)butyl]propanamide [prepared in Example 39(e), 1.034 g., 2.95 mmol.] in 6 mL of degassed water at room temperature under argon was added a mixture of concentrated NH4OH (1.95 mL) and water (1.95 mL). After two minutes, the reaction was quenched with saturated potassium bisulfate (pH 1.5) and extracted with ethyl acetate. The organic extracts were dried and purified by flash chromatography (50 mm×6 inch, 1:1 hexanes:ethyl acetate +0.5% acetic acid) to give 0.76 g. of white solid product. This material was combined with 25 mg. from a previous experiment and recrystallized from ethyl acetate/hexanes to give 0.69 g. of the title (S,S) isomer product as a white solid, m.p. 183°-184° C., TLC Rf =0.14 (1:1, hexanes:ethyl acetate +0.5% acetic acid). [α]D =-39.8° (c=0.57, methanol).

Provenance & Evidence