1,1'-Carbonyldiimidazole → HCID 86657120, compound

Participants

Reaction Steps

A cooled solution of (2S)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoic acid (3) (0.1 g, 0.32 mmol) and CDI (0.054 g, 0.33 mmol) in dry CH2Cl2 (5 mL) was stirred for 1 h at T=0-5° C. After ice-water bath removal, a mixture of D-alanine methyl ester hydrochloride (0.045 g, 0.32 mmol) and TEA (90 μl, 0.65 mmol) was added with vigorous stirring and the resulting mixture was stirred overnight at room temperature. At the complete disappearance of the starting material, a buffer H3PO4/H2PO4− solution (pH=2.0, 5 ml) was added and the reaction mixture was transferred into a separatory funnel. The two phases were separated and the organic one washed with the same buffer (3×5 mL), dried over Na2SO4 and evaporated under vacuum to give a crude which was purified by flash chromatography. Pure methyl (2R)-2-{[(2S)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoyl]amino}propanoate (0.1 g, 0.25 mmol) was isolated as a yellow oil (78%).

Provenance & Evidence