Propionic Acid → HCID 12052616, compound

Participants

Reaction Steps

To a solution of Compound 20b (10.0 mg, 3.50×10−2 mmol), DCC (7.2 mg, 3.50×10−2 mmol), and DMAP (8.5 mg, 6.99×10−2 mmol) in dry CH2Cl2 (4 mL) cooled in an ice-water bath was added propionic acid (3.8 mg, 5.24×10−2 mmol) followed by stirring at room temperature for 4 hours. The reaction mixture was filtered through a short plug of Celite with rinsing by EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 8.3 mg (69 percent) of Compound 36: pale yellow oil; Rf=0.43 (20 percent EtOAc in hexane); IR (neat) 2958, 2235, 1726, 1189, 1067 cm−1; 1H NMR (300 MHz, CDCl3) δ8.31 (d, J=7.23 Hz, 1H), 8.01 (d, J=7.56 Hz, 1H), 7.83 (t, J=8.01 Hz, 2H), 7.54-7.46 (m, 3H), 7.45 (s, 1H), 6.24 (s, 1H), 2.52-2.24 (m, 6H), 1.96-1.67 (m, 4H), 1.20 (t, J=7.56 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ174.5, 134.2, 133.0, 132.7, 132.2, 129.7, 129.3, 127.0, 127.0, 126.5, 126.0, 124.2, 123.8, 103.3, 93.6, 81.0, 79.5, 69.4, 28.5, 28.3, 28.2, 22.6, 21.5, 9.8; MS (+CI) m/z (relative intensity) 342 (M+, 5), 269 (100).

Provenance & Evidence