3-Hydroxypropionic acid → 3-(4-(1-(3-Hydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one

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To a solution of 3-hydroxypropionic acid (45 mg, 0.5 mM) in N,N-dimethylformamide (2 ml) was added 3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxy-carbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride (256 mg, 0.5 mM, reference example 10), and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (190 mg, 0.5 mM). The mixture was cooled to 0°, N,N-diisopropylethylamine (129 mg, 1 mM) added, and the mixture stirred 18 hours, allowing the temperature to rise to ambient. The mixture was poured into a mixture of ethyl acetate (40 ml) and water (40 ml), the organic layer separated and washed with aqueous sodium dihydrogen phosphate (2%, 40 ml), sodium bicarbonate (40 ml) and brine (40 ml). Solvent was removed, and the residue chromatographed on a 10 g silica Mega Bond Elut® column, eluting with a mixture of 2.5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the title product (203 mg). NMR (DMSO-d6) δ: 1.47 (s, 9H); 2.28 (m, 1H); 2.37 (m, 1H); 2.54 (m overlapped by DMSO, 2H); 3.66 (br m, 4H); 3.86 (dd, 1H); 3.95 (dd, 1H); 4.08 (m, 1H); 4.17 (m, 1H); 4.26 (dd, 2H); 4.53 (m, 1H); 5.02 (m, 1H); 5.87 (s, 1H); 6.86 (s, 1H); 7.33 (d, 2H); 8.82 (s, 1H). MS (ESP): 549 (MH+) for C26H30F2N4O7

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