Ethanol → HCID 67191160, compound

Participants

Reaction Conditions

Reaction Steps

In a flask containing (R)—N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-2-(4-methanesulfonyl-3-methyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionamide (100 mg, 0.18 mmol) was added ethanol (3 mL) and concentrated hydrochloric acid (three drops) and it was stirred at 25° C. for 45 min. It was then diluted with acetonitrile and absorbed onto silica gel (2 g) in vacuo and purified on Biotage Flash chromatography system (40S column, silica gel, 80% ethyl acetate/hexanes to 10% methanol/ethyl acetate) to afford (R)—N-[1-(2-hydroxy-ethyl)-1H-pyrazol-3-yl]-2-(4-methanesulfonyl-3-methyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionamide (55 mg, 69%) as a yellow foam: [α]32589=−73.6° (c=0.14, methanol); ES-HRMS m/e calcd for C21H27N3O5S (M+H)+ 434.1745, observed 434.1745; 1H NMR (400 MHz, DMSO-d6) δ 1.51 (m, 1H, CH), 1.77-2.28 (m, 8H, 4×CH2), 2.63 (s, 3H, ArCH3), 3.18 (s, 3H, SO2CH3), 3.67 (q, J=5.5 Hz, 2H, OCH2), 3.91 (m, 1H, ArCHCO), 3.99 (t, J=5.5 Hz, 2 H, NCH2), 4.82 (t, J=5.5 Hz, 1H, OH), 6.41 (d, J=2.2 Hz, 1H, Ar), 7.46 (brs, 1H, Ar), 7.47 (brd, 1H, Ar), 7.53 (d, J=2.2 Hz, 1H, Ar), 7.86 (d, Jo=8.5 Hz, 1H, Ar), 10.77 (s, 1H, NH).

Provenance & Evidence