反应详情

To a THF:MeOH:H2O (3:2:1) (3 mL) solution of 2-[(2,4-Dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester (30 mg, 0.076 mmol), 1N aqueous solution of lithium hydroxide (0.46 mL, 0.46 mmol) was added and the reaction mixture was stirred at room temperature for 6 h. Solvents were removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The water layer was acidified using 10% KHSO4 solution and then the organic layer was separated, dried (Na2SO4), concentrated. The residue was purified by column chromatography (ethyl acetate:hexane 1:1 to ethyl acetate) to obtain 2-[(2,4-dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid, 23 mg (81%) as a white solid. The compound contains two other minor rotamers. 1H NMR (CDCl3, 400 MHz): δ7.45-7.05 (m, 8H), 6.77 (dd, minor rotamer), 5.70 (d, minor rotamer), 4.99 (bs, minor rotamer), 4.64-4.59 (m, minor rotamer), 4.28 (d, minor rotamer), 4.29-4.18 (m, minor rotamer), 3.79-3.09 (m, 5H), 2.37 (t, minor rotamer), 2.31 (t, minor rotamer), 2.17 (t, 1H). ESI− (M−H): 375.

1. customSolvents were removed under reduced pressure
2. customthe residue was partitioned between ethyl acetate and water
3. customthe organic layer was separated
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customThe residue was purified by column chromatography (ethyl acetate:hexane 1:1 to ethyl acetate)