2-Aminothiazole → (S)-3-Cyclohexyl-2-(4-methylsulfonyl-1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide

Participants

Reaction Steps

BOP coupling of (S)-3-cyclohexyl-2-(4-methylsulfonyl-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid and regio-isomeric (S)-3-cyclohexyl-2-(7-methylsulfonyl-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (112 mg; 0.31 mmol) and 2-aminothiazole (54 mg; 0.52 mmol) in a manner similar to that used for the preparation of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (outlined in Example 9, Step B) provided after flash chromatography (Biotage 40M; eluent: ethyl acetate/methylene chloride: gradient 15%-50% ethyl acetate) provided 51 mg (S)-3-Cyclohexyl-2-(4-methylsulfonyl-1-oxo-1,3dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide: EI-HRMS m/e calcd for C21H25N3O4S2 (M+−2) 445.1130, found 445.1125 and 39 mg of (S)-3-Cyclohexyl-2-(7-methylsulfonyl-1-oxo-1,3dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide: EI-HRMS m/e calcd for C21H25N3O4S2 (M+) 447.1286, found 447.1280.

Provenance & Evidence