Hydrochloric Acid → (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide

Participants

Reaction Steps

A solution of (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-amide (prepared in Example 252, 600 mg, 1.16 mmol) in tetrahydrofuran (25 mL) was treated with 2N aqueous hydrochloric acid (12 mL) and stirred at room temperature for 2 h. At this time the mixture was concentrated in vacuo and the residue partitioned between 17% ethyl acetate/hexanes and water. The layers were separated and the organic layer was washed with brine and dried with sodium sulfate. The mixture was filtered and concentrated in vacuo which afforded (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide (500 mg, 90.4%) as a fluffy powder: HR-ES-MS (m/z) calculated for C23H29ClN4O5 [M+H]+ 477.1899, observed 477.1896. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.86 (br. s., 3H), 1.29 (br. s., 6H), 1.78 (br. s., 2H), 3.14-3.58 (m, 4H), 3.70-3.93 (m, 2H), 4.09 (dd, J=13.4, 2.6 Hz, 1H), 4.21 (d, J=18.4 Hz, 1H), 4.58 (d, J=18.4 Hz, 1H), 4.69-4.79 (m, 1H), 4.79 (s, 1H), 6.41 (br. s., 1H), 7.37 (t, J=7.2 Hz, 1H), 7.41-7.58 (m, 3H), 7.65 (d, J=7.8 Hz, 1H), 10.70 (br. s., 1H).

Provenance & Evidence