HCID 68752619, compound → 2-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid

Participants

Reaction Steps

A suspension of tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoate (81.2 mg, 0.148 mmol) and Pd/C (31.5 mg, 0.015 mmol) in EtOH (1 ml) was allowed to stir under hydrogen atmosphere (1 atm) for 6.5 hr. The reaction mixture was filtered, and the filter cake was washed with MeOH. The combined filtrate was concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN) to give 2-(1-(3-tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid (30.6 mg); Retention time=1.30 minutes (condition B); MS (m+1)=458.2; 1H NMR (400 MHz, CDCl3, data for major rotamer) δ ppm 1.37 (s, 9H) 1.70-1.98 (m, 8H) 2.64-2.88 (m, 5H) 3.34-3.53 (m, 2H) 6.53-6.56 (m, 1H) 7.02-7.04 (m, 1H) 7.28 (d, J=2.0 Hz, 1H) 7.36 (d, J=8.0 Hz, 1H).

Provenance & Evidence