(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine → (3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[N-[5-(allyloxycarbonylaminomethyl)imidazo[5,1-b]thiazol-3-yl]methyl-N-methylaminocarbonyl]pyrrolidine

Participants

Reaction Steps

The procedure of Synthesis Example 1 is repeated, except that 255 mg of (3S,5S)-3-acetylthio-1-allyloxycarbonylpyrrolidin-5-carboxylic acid, 0.93 ml of a 1.1 M Vilsmeier reagent/dichloromethane solution, and 262 mg of 5-allyloxycarbonylaminomethyl-3-(N-methylamino-methyl)imidazo[5,1-b]thiazole are used and 0.145 ml of triethylamine is finally added at 4° C. followed by stirring at room temperature for additional 50 min. Thus, 327.5 mg of the title compound is prepared as a colorless amorphous material.

Provenance & Evidence