1,3-Thiazole-5-carbaldehyde → HCID 66875151, compound

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Reaction Steps

The title compound, m/e=384.3 ([M+H]+), was produced in analogy with example 43, steps 1 to 4. Thus, thiazole-5-carboxaldehyde was reacted in step 1 with (8-carboxy-octyl)-triphenyl-phosphonium bromide, leading to 10-(thiazol-5-yl)-dec-9-enoic acid. In step 2, this was converted to 10-(thiazol-5-yl)-dec-9-enoyl chloride, then reacted with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride, leading to (R)-4-dimethylamino-3-[10-(2,3-difluoro-phenyl)-dec-9-enoylamino]-butyric acid benzyl ester. In step 3, reaction of (R)-4-dimethylamino-3-[10-(2,3-difluoro-phenyl)-dec-9-enoylamino]-butyric acid benzyl ester with triethylsilane-trifluoroacetic acid produced 4-dimethylamino-3-(10-thiazol-5-yl-decanoylamino)-butyric acid benzyl ester, which was hydrolyzed in step 4.

Provenance & Evidence