[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14]NCC(O)CO)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].COC(C1N=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]([OH:45])[CH2:39]NC(C)(C)C)=[CH:32][CH:31]=2)NC=1)=O.[OH2:46]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][CH2:39][CH:38]([OH:45])[CH2:37][O:36][C:33]2[CH:34]=[CH:35][C:30]([CH:27]=[O:46])=[CH:31][CH:32]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]To a suspension of NaH (60% oil dispersion, 1.2 g, 0.03 mol) in DMF (20 ml) was added at 70° C. under N2 a solution 3 (37 g, 0.03 ml) in DMF (30 ml). After stirring for 15 minutes at 70° C. a solution of (S) 2 in DMF (50 ml) was added dropwise. After the addition, the mixture was heated at 120° C. for 18 hours. The solution was then poured into H2O and extracted with EtOAc (3X). The organic extracts were washed with H2O (2X), saturated NaCl (1X), dried, filtered and concentrated to dryness. The residue was treated with H2O (250 ml) and AcOH (25 ml) and stirred overnight at room temperature. The solution was extracted with EtOAc (2X), neutralized with saturated Na2CO3 and extracted with CHCl3 (9X). The organic extracts were dried, filtered and concentrated to yield 8.5 g of 4; 'H NMR (CDCl3) δ 2.7 (6H, m), 3.8 (6H, s), 4.1 (3H, m), 6.7 (3H, bs), 6.95 (2H, d), 7.75 (2H, d). ##STR152##
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