[N:1]1[NH:2][CH:3]=[C:4]2[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C:5]=12.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O1[CH2:30][CH2:29]CC1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].CN(C)C=[O:39]>>[C:4]1([S:32]([OH:34])(=[O:39])=[O:33])[CH:5]=[CH:6][CH:30]=[CH:29][CH:8]=1.[CH3:31][S:32]([N:2]1[CH:3]=[C:4]2[CH2:8][NH:7][CH2:6][C:5]2=[N:1]1)(=[O:34])=[O:33]A solution of the product from Step B (100 g, 478 mmol) in anhydrous N,N-dimethylformamide (1.0 L) was cooled to −40° C. and treated with 1 M sodium bis(trimethylsilyl)amide in tetrahydrofuran (502 mL, 502 mmol) slowly over 20 min. The temperature warmed to −30° C. during the addition and the mixture was stirred at this temperature for 1 h. Methanesulfonyl chloride (44.7 mL, 573 mmol) was slowly added via addition funnel and stirred for an additional 1.5 h at −30 to −40° C. The reaction mixture was quenched with ice (3.5 kg), slowly warmed to ambient temperature and stirred for 48 h. The resulting white solid was filtered, washed with water and suction dried to afford the title compound. LC/MS: 288.1 (M+1).
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