Acetone → HCID 68752581, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)—N-(3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-yl)-1-(2-chloroallyl)cyclopentanecarboxamide (38 mg, 0.09 mmol) in acetone (5 mL) at −78° C. was bubbled ozone for 1 minute with a persistent pale blue color. The mixture was stirred at −78° C. for 5 minutes. To the mixture was bubbled oxygen for 10 minutes then added dimethyl sulfide (0.5 mL) followed by 1 mL of water. The mixture was stirred for 1 hr at room temperature and concentrated under reduced pressure. The obtained mixture was diluted in EtOAc and acidified with 1 M HCl. The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained residue was purified with RP-HPLC (SunFire C8, H2O (0.1% TFA)/CH3CN) to give (S)-2-(1-(3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamoyl)cyclopentyl)acetic acid (27 mg). HPLC retention time=1.44 minutes (condition B); MS (m+1)=409.0; 1H NMR (400 MHz, ACETONITRILE-d3) δ ppm 1.33-1.63 (m, 6H), 1.72-1.94 (m, 2H), 2.60 (d, J=16.4 Hz, 1H), 2.73 (d, J=4.8 Hz, 3H), 2.73 (d, J=16.4 Hz, 1H), 2.97 (dd, J=14.1, 10.4 Hz, 1H), 3.39 (dd, J=14.1, 4.5 Hz, 1H), 4.58-4.76 (m, 1H), 6.70 (d, J=7.6 Hz, 1H), 7.09 (br. s., 1H), 7.34 (d, J=8.3 Hz, 2H), 7.38 (t, J=7.3 Hz, 1H), 7.43-7.51 (m, 2H), 7.59 (d, J=8.1 Hz, 2H), 7.62-7.67 (m, 2H).

Provenance & Evidence