HCID 10374773、化合物 → 3-(4-(3(S)-(2(S),3-Dihydroxypropanoyl)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

関与物質

反応手順

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.698 mM) in pyridine (5 ml) was treated dropwise with a solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (200 mg, 1.2 mM) in dichloromethane (2 ml), and the mixture stirred 3 hours at ambient temperature. The mixture was diluted with ethyl acetate (15 ml) and water (15 ml), the organic layer separated, washed with aqueous sodium bicarbonate (10 ml) and brine (10 ml), and evaporated, then azeotroped with toluene (20 ml). The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (435 mg ). NMR (DMSO-d6) δ: 1.30 (s, 3H); 1.37 (s, 3H); 1.89 (hextet, 1H); 2.13 (hextet, 1H); 3.20 (m, 1H); 3.24 (m overlapped by H2O, ˜1H); 3.39 (m, 1H); 3.48 (m, 1H); 3.82 (dd, 1H); 3.91 (dd, 1H); 4.12 (overlapping m, 3H); 4.33 (t overlapping m, 2H); 4.42 (dd, 2H); 4.97 (d, 1H); 5.02 (m, 1H); 5.06 (d, 1H); 6.75 (t, 1H); 6.87 (d, 1H); 7.08 (dd, 1H); 7.34 (dd, 1H); 7.94 (d, 1H); 8.89 (d, 1H). MS (ESP): 664 (MH+) for C26H29Cl3FN5O8

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