Trifluoroacetic acid → HCID 57835925, compound

Participants

Reaction Steps

TFA (10 mL) was added to 76.4 (940 mg) in DCM (10 mL). The mixture was stirred at room temperature for 1.5 hours. TFA and DCM were removed under vacuum, and the residue was treated with EtOH (50 mL). The insoluble solid was removed by filtration. To the filtrate was added concentrated sulfuric acid (2 drops). The mixture was stirred at 80° C. overnight. After concentration, the crude product was purified by flash chromatography to give 76.5 (410 mg). MS ESI (pos.) m/e: 262 (M+H). 1HNMR (CDCl3) δ 8.29 (d, 1H), 7.12 (d, 2H), 6.76 (d, 2H), 6.10 (d, 1H), 4.56 (t, 1H), 4.10(q, 2H), 3.27 (dd, 1H), 2.97 (dd, 1H), 1.19 (t, 3H). The racemic compound 76.5 was separated into two enantiomers 76.6 and 76.7 using chiral preparative AD-H column (8% IPA/92% hexanes). The stereochemistry of 76.6 and 76.7 was assigned arbitrarily.

Provenance & Evidence