[Br:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].[Cl:13][CH2:14][CH2:15][CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH2:15][CH2:14][Cl:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]A suspension of Example 106D (250 mg, 1.1 mmol), 3-chloropropanol (0.095 mL, 1.1 mmol), and triphenylphosphine (350 mg, 1.3 mmol) in dichloromethane (5 mL) at 0° C., was treated dropwise with DEAD (0.21 mL, 1.3 mmol) over 10 minutes. The resulting mixture was stirred at 0° C. for 1 hour, warmed to room temperature overnight, and concentrated. The residue was purified by silica gel chromatography with 50 to 60% ethyl acetate/hexanes to give 227 mg of the desired product which was contaminated with triphenylphosphine oxide. MS (ESI(+)) m/e 304,306 (M+H)+.
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