반응 #47688
ord-f003766450d34b18912f53af32e906ea
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후처리
- 1기타At this time the mixture was partitioned between ethyl acetate and water
- 2기타The layers were separated
- 3추출the aqueous layer was extracted with ethyl acetate
- 4세척The combined organic layers were washed with brine
- 5건조dried over sodium sulfate
- 6여과The mixture was filtered
- 7농축concentrated in vacuo
- 8기타the residue was purified by ISCO flash chromatography (RediSep silica column 12 g, 30% to 80% (10% methanol/dichloromethane)hexanes) which
실험 절차
A solution of (S)-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 (360 mg, 0.7 mmol) in tetrahydrofuran (15 mL) was treated with 2N aqueous hydrochloric acid (7.5 mL) and stirred at room temperature for 2.5 h. At this time the mixture was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. The mixture was filtered and concentrated in vacuo and the residue was purified by ISCO flash chromatography (RediSep silica column 12 g, 30% to 80% (10% methanol/dichloromethane)hexanes) which afforded (S)-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 (285 mg, 86%) as a white fluffy solid: HR-ES-MS (m/z) calculated for C23H29ClN4O5 [M+H]+ 477.1899, observed 477.1897. 1H NMR showed mixture of diastereomers (400 MHz, DMSO-d6) δ ppm 0.77-0.96 (m, 6H), 1.04-1.93 (m, 5H), 3.23-3.33 (m, 2H), 3.77 (br. s., 1H), 3.82-3.91 (m, 1H), 4.04-4.14 (m, 1H), 4.11-4.29 (m, 1H), 4.58, 4.63 (2×d, J=18.7 Hz, 1H), 4.71 (br. s., 1H), 4.79, 4.81 (2×s, 1H), 4.86-4.97 (m, 2H), 6.42 (br. s., 1H), 7.37 (t, J=7.7 Hz, 1H), 7.46 (t, J=7.5 Hz, 1H), 7.49-7.56 (m, 2H), 7.65 (d, J=7.9 Hz, 1H), 10.77, 10.79 (2×s, 1H)