Trifluoroacetic acid → HCID 51354736, compound

Participants

Reaction Steps

To a solution of crude t-butyl 1-(((2R)-2-(4-(2-methylpentyloxy)phenyl)-2-((S)-2-phenylpropanamido)ethylamino)methyl)cyclopentylcarbamate from Part A (195 mg, 0.345 mmol) in dichloromethane (2 mL) at 0° C. was added TFA (1 mL, 12.98 mmol). The reaction mixture was stirred for 1.5 h while being allowed to warm to room temperature. The mixture was concentrated and the product was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA). The organic solvent was removed on the rotovapor and the aqueous mixture was frozen and placed on the lyophilizer to afford (2S)-N-((1R)-2-((1-aminocyclopentyl)methylamino)-1-(4-(2-methylpentyloxy)phenyl)ethyl)-2-phenylpropanamide (154 mg, 63% yield, 2 steps) as a colorless amorphous solid: 1H NMR (300 MHz, 100° C., DMSO-d6) δ 7.95 (d, J=8.1 Hz, 1H), 7.16-7.34 (m, 5H), 7.11 (d, J=8.4 Hz, 2H), 6.81 (d, J=8.8 Hz, 2H), 6.87 (br. s., 5H), 4.94-5.06 (m, 1H), 3.68-3.88 (m, 3H), 2.96-3.13 (m, 2H), 2.93 (s, 2H), 1.59-1.95 (m, 9H), 1.40 (d, J=7.0 Hz, 3H), 1.17-1.49 (m, 4H), 0.97 (d, J=7.0 Hz, 3H), 0.90 (t, J=7.0 Hz, 3H); HPLC tR=2.68 min (Method A); LRMS (ESI) m/e 466.5 [(M+H)+, calcd for C29H44N3O2 466.4].

Provenance & Evidence