Imidazole → HCID 59193079, compound

Participants

Reaction Steps

A 500 mL round bottomed flask was charged with N′-((2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)-1H-indole-5-carbohydrazide (1.94 g, 4.56 mmol) and DMF (200 mL). Imidazole (1.55 g, 22.78 mmol) and tert-butyldimethyl silyl chloride (2.06 g, 13.68 mmol) were then added to the mixture which was stirred at room temperature for 18 h. Water (80 mL) was added to the mixture followed by EtOAc (150 mL). The phases were partitioned and the organic phase washed with water (70 mL) (×4), brine (50 mL), dried (Na2SO4) and concentrated to furnish a white solid. Purification by flash column chromatography [EtOAc-hexanes) as eluent] afforded the title compound as a colorless oil (4.58 g, 35% yield). 1H NMR (500 MHz, acetone d6, δ in ppm) δ 10.51 (br s, 1H), 9.5 (br s, 1H), 8.22 (br s, 1 H), 7.70 (d, J=8.41 Hz, 1H), 7.55-7.47 (m, 2 H), 7.44-7.42 (m, 1H), 6.77 (d, J=8.6 Hz, 1 H), 6.58-6.56 (m, 1H), 5.51 (d, J=7 Hz), 4.63-4.55 (m, 1H), 4.23-4.19 (m, 1H), 2.36 (s, 3H) and 1.36 (d, J=6.23 Hz, 3H), 0.95 (s, 9 H), 0.17 (s, 3 H) and 0.13 (s, 3H).

Provenance & Evidence