Pentamethylbenzene → HCID 53276190, compound

Participants

Reaction Steps

To a solution of tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(3,5-dichlorobenzyl)propanoate (130 mg, 0.237 mmol) in TFA (1.5 ml), pentamethylbenzene (351 mg, 2.370 mmol) was added at room temperature. After stirred for 2 hr, the reaction mixture was concentrated under reduced pressure. The obtained crude material was hydrogenated under hydrogen atmosphere (1 atm) with Pd/C in EtOAc for 0.5 hr at room temperature. The reaction mixture was filtered, and the filtered cake was washed with MeOH. The combined filtrate was concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (SunFire, H2O (0.1% TFA)/CH3CN) to give 341-(carboxymethyl)cyclopentanecarboxamido)-2-(3,5-dichlorobenzyl)propanoic acid (62.5 mg); Retention time=0.71 minutes (condition B); MS (m+1)=402.0; 1H NMR (400 MHz, DMSO-6, mixture of rotamers) δ ppm 1.47-1.58 (m, 6H) 1.95-2.05 (m, 2H) 2.54-2.63 (m, 2H) 2.68-2.85 (m, 3H) 3.13-3.29 (m, 2H) 7.24 (d, J=1.8 Hz, 2H) 7.42-7.43 (m, 1H) 7.60-7.63 (m, 1H); HRMS (ES+) m/z for C18H22Cl2NO5 [M+H]+ calcd 402.0875. found 402.0854

Provenance & Evidence