[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:3][CH2:2]1.Cl[Si](C)(C)C>CO>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)(=[O:15])=[O:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:2][CH2:3]1To a solution of tert-butyl 4-((1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)methyl)piperidine-1-carboxylate (STEP C, 1.39 g, 2.76 mmol) in methanol (15 mL) was added chlorotrimethylsilane (1.41 mL, 11.0 mmol). After stirring for 18 h, the mixture was concentrated in vacuo. The residue was diluted ethyl acetate and basified with saturated sodium bicarbonate aqueous solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate and concentrated to give the title compound (809 mg, 73%) as an amorphous.
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