[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)C(O)=O.C[N:12]1[CH2:17]COCC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCCl>[CH2:35]([O:42][C:17](=[O:25])[NH:12][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([F:1])[CH:10]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
The product of Example 224A (1.00 g, 7.087 mmol) and N-methylmorpholine (0.86 mL, 7.796 mmol) in anhydrous 1,2-dichloroethane (30 mL) was stirred under a nitrogen atmosphere for 10 minutes at room temperature. Diphenyl phosphoryl azide (1.68 mL, 7.796 mmol) was then added dropwise and the reaction stirred for 30 minutes at the same temperature. The reaction was then slowly heated to 75° C. over a 20-minute period and was maintained at this temperature for 1 hour. Benzyl alcohol (1.10 mL, 10.63 mmol) and cuprous chloride (20 mg) were added and the reaction was refluxed for 3 hours. The reaction was then cooled to room temperature and the solvent removed by rotary evaporation in vacuo. Purification by silica gel chromatography eluting with 20% ethyl acetate/methylene chloride afforded the title compound as an off-white solid (718 mg, 41%).
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