F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)(=[O:13])=[O:12].CS(CCO)(=O)=[O:22].[H-].[Na+]>CN(C=O)C>[OH:22][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)(=[O:13])=[O:12]4-Fluoro-3-(morpholine-4-sulfonyl)-benzoic acid (Example 6, 5.36 g, 19 mmol) was dissolved in DMF and commercially available 2-methylsulfonyl ethanol (4.8 g, 39 mmol) was added. After five minutes of stirring, sodium hydride (2.4 g of 60% dispersion in mineral oil, 61 mmol) was added. The solution immediately turned black. After 15 min, the reaction was complete. The DMF solution was partitioned between ethyl acetate (150 mL) and brine/HCl (200 mL). The brine solution was discarded, and this was repeated two additional times. All ethyl acetate was dried with magnesium sulfate, and removed under reduced pressure to provide the title compound as a white solid (4.0 g, 74%): 1HNMR (DMSO-d6) δ8.23 (d, J=2 Hz, 1H), 8.02 (dd , J=9 Hz, 2 Hz, 1H), 7.09 (d, J=9 Hz, 1H), 3.62 (m, 4H), 3.12 (m, 4H); MS (−APCI):[M−H]−286; Anal.Calc. for C11H13NO6S: C, 44.99; H, 4.56; N, 4.88. Found: C, 45.45; H, 4.41; N, 4.74.
Wird geladen…
