Diethyl Ether → HCID 54671228, compound

Participants

Reaction Steps

To a solution of [1-[4-[2-[3-[bis(tert-butoxycarbonyl)amino]-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]ethynyl]phenyl]-2-(tert-butoxycarbonylamino)ethyl]tert-butyl carbonate (250.3 mg, 0.2990 mmol) in DCM (2.503 mL) was added TFA (1 mL, 12.98 mmol) and the mixture was stirred at ambient temperature for 18 hours. After this time ether was added to the reaction mixture, the precipitate which resulted was isolated by filtration and dried under vacuum. The filtrate was recombined with precipitate and re-dissolved in DCM. Polymer supported 3-Mercaptopropyl ethyl sulfide was added to the solution and this was left to stir for 15 minutes at ambient temperature. After this time the resin was removed by filtration and washed with DCM. The filtrate was concentrated in vacuo and the material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge to give the titled product as a solid (15.01 mg, 11.5% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, J=6.8 Hz, 6H), 2.65 (dd, J=8.1, 12.8 Hz, 2H), 3.45 (t, J=6.8 Hz, 1H), 4.58 (dd, J=3.7, 7.9 Hz, 1H), 5.60 (br s, 1H), 7.15 (s, 2H), 7.43 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.2 Hz, 2H), 7.91 (d, J=8.5 Hz, 2H), 8.24 (d, J=8.5 Hz, 2H) and 8.75 (s, 1H) ppm; MS (ES+) 437.1.

Provenance & Evidence