Cesium carbonate → (S)-3-((S)-3-(4-(4-Bromo-3-(trifluoromethoxy)benzyloxy)-phenyl)-3-(isoxazol-3-yl)propanoyl)-4-benzyloxazolidin-2-one

A mixture of 28.3 (1.30 g, 4.80 mmol), thionyl bromide (1.01 g, 4.84 mmol), and DMF (0.1 mL) in DCM (8.0 mL) was stirred at room temperature for 50 minutes. The solvent was then removed. To the residue was added 7.5 (1.10 g, 2.80 mmol) and Cs2CO3 (1.10 g, 3.36 mmol) in DMF (8.0 mL). The mixture was stirred at room temperature for 4 hours. EtOAc (150 mL) was added, and the mixture was washed with brine (25×3 mL) and dried with MgSO4. The solvent was removed, and the crude product was purified by CombiFlash, eluting with EtOAc and hexane, to give the title compound 28.4. 1H NMR (CDCl3) δ 2.77 (dd, J=4.2, 9.5 Hz, 1H), 3.21 (dd, J=4.2, 9.5 Hz, 1H), 3.52 (dd, J=8.6, 17.6 Hz, 1H), 4.04 (dd, J=8.6, 17.6 Hz, 1H), 4.63 (m, 1H), 4.76 (m, 1H), 5.01 (s, 2H), 6.14 (d, J=1.5 Hz, 1H), 6.92 (d, J=6.9, Hz, 2H), 7.20-7.35 (m, 9H), 7.64 (d, J=8.3, Hz, 1H), 8.31 (d, J=1.5 Hz, 1H). MS ESI (pos.) m/e: 647 (M+H).

1. customThe solvent was then removed
2. stirringThe mixture was stirred at room temperature for 4 hours
3. washthe mixture was washed with brine (25×3 mL)
4. dry with materialdried with MgSO4
5. customThe solvent was removed
6. customthe crude product was purified by CombiFlash
7. washeluting with EtOAc and hexane

ORD-Eintrag

ord-f089181fa7a94b4a84a653d1a88ba779

Quelldatensatz

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07714008B2