Acetyl chloride → Acetic acid 4-{(3R,4S)-3-(4-chloro-phenyl)-4-[ethyl-(4-fluoro-phenoxycarbonyl)-amino]-pyrrolidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-yl ester

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Reaction Steps

In analogy to the procedure described for the synthesis of [(3S,4R)-1-(5′-Cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carbonyl)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid 4-fluoro-phenyl ester (example 35, step f) the intermediate was prepared from [(3S,4R)-4-(4-Chloro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid 4-fluoro-phenyl ester and 1-(5-hydroxypyridin-2-yl)piperidine-4-carboxylic acid. Afterwards, acetyl chloride was added and stirring was continued for 30 min at room temperature. The mixture was directly subjected to preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield the title compound as off-white solid. MS m/e: 608.2 [M+H]+.

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