Carboxamide for Treatment of Hepatitus C
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CH2Cl2 and washed with saturated NaHCO3, and brine. The organic
layer was dried (MgSO4), filtered, concentrated in vacuo, and
purified by chromatography (SiO2, acetone/hexanes, 3:7) to yield
1
70 as a colorless solid as a mixture of diasteromers. H NMR
(DMSO-d6, 500 MHz) δ 8.26 (d, 1 H, J ) 7.0 Hz), 8.00 (s, 1 H),
7.75 (s, 1 H), 5.96 (s, 1 H), 5.84 (d, 1 H, J ) 10 Hz), 4.96 (m, 1
H), 4.28 (s, 1H), 4.11 (d, 1 H, J ) 11 Hz), 3.94 (d, 1H, J ) 10
Hz), 3.73 (dd, 1 H, J ) 10 and 5 Hz), 2.48 (m, 1 H), 1.95 (m, 2
H), 1.61 (m, 1 H), 1.59 (m, 1 H), 1.77 (m, 1 H), 1.57 (m, 1 H),
1.74 (m, 2 H), 1.42 (dd, 1 H, J ) 7.5 and 5 Hz), 1.28 (d, 1 H, J )
7.5 Hz), 1.17 (s, 9 H), 1.01 (s, 3 H), 0.90 (s, 9 H), 0.85 (s, 3 H),
8.15 (d, 1 H, J ) 7.0 Hz), 7.96 (s, 1 H), 7.74 (s, 1 H), 5.96 (s, 1
H), 5.86 (d, 1 H, J ) 10 Hz), 4.85 (m, 1 H), 4.27 (s, 1H), 4.13 (d,
1 H, J ) 11.0 Hz), 3.97 (d, 1H, J ) 10 Hz), 3.76 (dd, 1 H, J ) 10
and 5 Hz), 2.36 (m, 1 H), 1.97 (m, 2 H), 1.60 (m, 2 H), 1.78 (m,
1 H), 1.64 (m, 1 H), 1.75 (m, 2 H), 1.44 (dd, 1 H, J ) 7.5 and 5
Hz), 1.27 (d, 1 H, J ) 7.5 Hz), 1.17 (s, 9 H), 1.00 (s, 3 H), 0.89
(s, 9 H), 0.82 (s, 3 H); 13C NMR (DMSO-d6, 125 MHz) δ 197.8,
170.9, 170.8, 162.8, 157.4, 59.1, 56.8, 51.8, 48.9, 47.4, 36.7, 34.0,
32.0, 30.6, 29.1, 27.8, 27.3, 27.1, 26.4, 26.1, 18.5, 17.7, 12.5. 197.1,
171.1, 170.7, 163.0, 157.3, 59.4, 56.9, 52.1, 48.9, 47.4, 36.6, 34.0,
32.1, 30.5, 29.1, 27.9, 27.4, 26.8, 26.4, 26.1, 18.5, 17.8, 12.4. HRMS
calcd for C27H46O5N5 [M + 1]+ 520.3499. Observed: 520.3514.
Anal Calcd for C27H45N5O5: C, 62.40%; H, 8.73%; N, 13.48%.
Found: C, 62.48%; H, 8.94%; N, 13.19%.
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Note Added after ASAP Publication. This manuscript was
released ASAP on September 7, 2006 with an error in an
author’s name. The correct version was posted on September
20, 2006.
Supporting Information Available: NMR and MS data for
compounds 26-74. This material is available free of charge via
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