Reaction SMILES: CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C@@H:25]12[CH2:30][C@@H:29]1[CH2:28][C@@H:27]([C:31]1[NH:32][C:33]([C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[CH:42]=[C:41]([C:46]3[CH:51]=[CH:50][C:49]([C:52]5[NH:56][C:55]([CH:57]6[CH2:62][C@@H:61]7[C@@H:59]([CH2:60]7)[N:58]6[C:63]([O:65][CH2:66][C:67]6[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=6)=[O:64])=[N:54][CH:53]=5)=[CH:48][CH:47]=3)[CH:40]=[CH:39]4)=[CH:34][N:35]=1)[NH:26]2.[CH3:73][O:74][C:75]([NH:77][C@@H:78]([CH:82]([CH3:84])[CH3:83])[C:79](O)=[O:80])=[O:76].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:73][O:74][C:75]([NH:77][C@@H:78]([CH:82]([CH3:84])[CH3:83])[C:79]([N:26]1[C@H:27]([C:31]2[NH:32][C:33]([C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[CH:42]=[C:41]([C:46]3[CH:47]=[CH:48][C:49]([C:52]5[NH:56][C:55]([CH:57]6[CH2:62][C@@H:61]7[C@@H:59]([CH2:60]7)[N:58]6[C:63]([O:65][CH2:66][C:67]6[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=6)=[O:64])=[N:54][CH:53]=5)=[CH:50][CH:51]=3)[CH:40]=[CH:39]4)=[CH:34][N:35]=2)[CH2:28][C@@H:29]2[C@H:25]1[CH2:30]2)=[O:80])=[O:76]
Reactant: O=C(OCc1ccccc1)N1C(c2ncc(-c3ccc(-c4ccc5cc(-c6cnc([C@@H]7C[C@H]8C[C@H]8N7)[nH]6)ccc5c4)cc3)[nH]2)C[C@H]2C[C@H]21
Reactant: COC(=O)N[C@H](C(=O)O)C(C)C
Agent: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: F[P-](F)(F)(F)(F)F
Solvent: CN(C)C=O
Solvent: CCN(C(C)C)C(C)C
Product: COC(=O)N[C@H](C(=O)N1[C@@H]2C[C@@H]2C[C@H]1c1ncc(-c2ccc3cc(-c4ccc(-c5cnc(C6C[C@H]7C[C@H]7N6C(=O)OCc6ccccc6)[nH]5)cc4)ccc3c2)[nH]1)C(C)C
Temperature: 25 °C
Reaction time: 3 h
Yield: 71.2 %

Procedure:
HATU (203 mg, 0.533 mmol) was added to a stirred solution of (1R,5R)-benzyl 3-(5-(4-(6-(2-((1R,3S,5R)-2-azabicyclo[3.1.0]hexan-3-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (225 mg) and (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (93 mg, 0.53 mmol) in DMF (3 mL) and DIPEA (0.37 mL, 2.1 mmol) and the reaction was stirred at rt for 3 hr. The crude reaction was concentrated under a stream of nitrogen and the residue was dissolved into MeOH and purified by preparative HPLC (MeOH/water with an ammonium acetate buffer) to yield (1R,5R)-benzyl 3-(5-(4-(6-(2-((1R,3S,5R)-2-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-2-azabicyclo[3.1.0]hexan-3-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (200 mg) as a yellow solid. LC-MS retention time 4.053 min; m/z 790.25 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and Solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. 1H NMR (400 MHz, MeOD) δ ppm 8.28 (s, 2H), 8.13 (d, J=8.8 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 7.94-8.02 (m, 4H), 7.76-7.92 (m, 3H), 7.85 (dd, J=8.7, 1.6 Hz, 1H), 7.29 (br. s., 5H), 5.21 (d, J=12.1 Hz 1H), 5.16 (dd, J=9.2, 6.9 Hz, 1H), 4.97 (t, J=8.2 Hz, 1H), 4.57 (d, J=6.5 Hz, 1H), 3.78-3.87 (m, 1H), 3.68 (s, 3H), 3.64-3.77 (m, 2H), 2.66-2.77 (m, 2H), 2.40-2.56 (m, 2H), 2.14-2.25 (m, 1H), 2.05-2.14 (m, 1H), 1.87 (d, J=6.5 Hz, 1H), 1.06-1.16 (m, 1H), 1.02 (d, J=6.8 Hz, 3H), 0.94 (d, J=6.8 Hz, 3H), 0.87-0.99 (m, 2H), 0.74-0.82 (m, 1H).