Triethylamine → HCID 70242261, compound

Participants

Reaction Steps

To a mixture of 2-[2-methyl-3(S)-(4-cyanophenyl)-isoxazolidin-5(R)-yl]acetic acid (500 mg, 2.0 mmol), b-alanine methyl ester HCl salt (314 mg, 2.4 mmol) and triethylamine (1.7 ml, 12 mmol) in DMF (7 ml), cooled with ice-water, was added PyBOP (1,18 g, 2.0 mmol). After stirring for 12 hrs, the reaction mixture was diluted with ethyl acetate and washed with dilute NaHCO3 and brine, then dried. Concentration followed by chromatography with a mixture of EtOAc and hexane as the eluent gave the product as an amorphous solid (660 mg, 98% yield).1H NMR (300 MHz, CDCl3) δ2.00 (m, 1H), 2.40(dd, 1H), 2.56(t, 2H), 2.60(s, 3H), 2.68(dd, 1H), 2.94(m, 1H), 3.54(qt, 2H), 3.68(t, 1H), 3.70(s, 3H), 4.60(m, 1H), 6.60(s, 1H), 7.46(d, 2H), 7.64(d, 2H); MS (ESI) Calc. for (M+1)+: 332. Found: 332.

Provenance & Evidence