Diisopropylethylamine → HCID 67503776, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask under argon was placed (S)-4-(t-butyl-dimethyl-silanyloxy)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-butyric acid (190 mg, 0.45 mmol) and 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-ylamine (prepared as in Example 49, 105 mg, 0.54 mmol) in N,N-dimethylformamide (3 mL). To this mixture was added N,N-diisopropyethylamine (220 μL, 1.34 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (295 mg, 0.57 mmol) and stirred for 5 h at 25° C. After this time, the mixture was diluted with ethyl acetate (25 mL) and washed with a saturated aqueous solution of ammonium chloride (25 mL), saturated aqueous solution of sodium bicarbonate (25 mL) and saturated aqueous sodium chloride solution (25 mL) dried over sodium sulfate, and concentrated in vacuo with silica gel (2 g). Purification by Biotage flash chromatography (Aspire 40 g column, 80% ethyl acetate/hexanes) afforded (S)-4-(t-butyl-dimethyl-silanyloxy)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-butyramide (131 mg, 49%) as a white foam: HR-ES-MS m/z calculated for C29H41N4O6ClSi [M+H]+ 605.2557, observed 605.2559.

Provenance & Evidence