Reaction SMILES: [CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:56]([CH3:58])[CH3:57])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:18][C:17]2[CH:19]=[C:20]([C:23]3[CH:55]=[CH:54][C:26]4[C:27]5[CH:33]=[CH:32][C:31]([C:34]6[NH:38][C:37]([C@@H:39]7[CH2:43][CH2:42][CH2:41][N:40]7C(OCC7C=CC=CC=7)=O)=[N:36][CH:35]=6)=[CH:30][C:28]=5[S:29][C:25]=4[CH:24]=3)[CH:21]=[CH:22][C:16]=2[N:15]=1)=[O:8])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:65][O:66][C:67]([NH:69][C@H:70]([C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)[C:71](O)=[O:72])=[O:68].CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F>O.C(O)C.[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:56]([CH3:58])[CH3:57])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:18][C:22]2[CH:21]=[C:20]([C:23]3[CH:55]=[CH:54][C:26]4[C:27]5[CH:33]=[CH:32][C:31]([C:34]6[NH:38][C:37]([C@@H:39]7[CH2:43][CH2:42][CH2:41][N:40]7[C:71](=[O:72])[C@H:70]([NH:69][C:67](=[O:68])[O:66][CH3:65])[C:74]7[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=7)=[N:36][CH:35]=6)=[CH:30][C:28]=5[S:29][C:25]=4[CH:24]=3)[CH:19]=[CH:17][C:16]=2[N:15]=1)=[O:8])=[O:4]
Reactant: COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1nc2ccc(-c3ccc4c(c3)sc3cc(-c5cnc([C@@H]6CCCN6C(=O)OCc6ccccc6)[nH]5)ccc34)cc2[nH]1)C(C)C
Reactant: COC(=O)N[C@@H](C(=O)O)c1ccccc1
Agent: [Pd]
Agent: CCOC(=O)C(C#N)=NOC(N1CCOCC1)=[N+](C)C
Agent: F[P-](F)(F)(F)(F)F
Solvent: CCO
Solvent: CCOC(C)=O
Solvent: O
Product: COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1nc2ccc(-c3ccc4c(c3)sc3cc(-c5cnc([C@@H]6CCCN6C(=O)[C@H](NC(=O)OC)c6ccccc6)[nH]5)ccc34)cc2[nH]1)C(C)C
Temperature: 0 °C
Reaction time: 18 h
Yield: 46.4 %

Procedure:
To a solution of (S)-benzyl 2-(5-(7-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-benzo[d]imidazol-6-yl)-dibenzo[b,d]thiophen-3-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (0.19 g, 0.24 mmol), potassium carbonate (70 mg, 0.50 mmol) and water (1 drop) in ethanol (3.5 mL) was added 10% palladium on carbon (175 mg). The reaction flask was flushed with argon for 2 minutes. Hydrogen gas was bubbled through the reaction mixture for 10 minutes. The reaction was stirred under hydrogen gas for 18 hours, and then flushed with argon. The mixture was diluted with methanol and filtered through Celite. The filtrate was concentrated and used without purification in the next step. This residue was dissolved in a 5:1 mixture of dichloromethane:dimethylformamide (3.0 mL) and cooled to 0° C. To the solution were sequentially added (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (76 mg, 0.36 mmol) and COMU (150 mg, 0.35 mmol). After one hour, the reaction was diluted with ethyl acetate and the organic layer was washed with water and brine. The combined aqueous washings were extracted three times with ethyl acetate, and the combined organic layers were dried (MgSO4) and concentrated. The crude material was purified by preparative reverse phase HPLC (Gemini, 15 to 50% ACN/H2O+0.1% TFA) to yield methyl (R)-2-((S)-2-(5-(7-(2-((S)-1-((S)-2-methoxycarbonylamino-3-methylbutanoyl)pyrrolidin-2-yl)-1H-benzo[d]imidazol-6-yl)dibenzo[b,d]thiophen-3-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate (95 mg, 47%). LCMS-ESI+: calculated for C47H48N8O6S: 853.00; observed [M+1]+: 853.85.