Reaction SMILES: [C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39](Br)[C:38]2=[N:43][C:35]3=[C:36](Br)[N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[C:26]([CH3:47])[C:27]([F:46])=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:52][S:53]([NH2:56])(=[O:55])=[O:54].C([O-])([O-])=O.[K+].[K+].O[Li].O>CN(C=O)C.[Cu]I.O>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([NH:56][S:53]([CH3:52])(=[O:55])=[O:54])[C:38]2=[N:43][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[C:26]([CH3:47])[C:27]([F:46])=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]
Reactant: COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(Br)c2nc3c(Br)n2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1cc(C)c(F)cc1-c1cccc-3c1
Reactant: CS(N)(=O)=O
Agent: [Cu]I
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: O
Solvent: CN(C)C=O
Product: Cc1cc2c(cc1F)-c1cccc(c1)-c1cn3c(c([C@H](OC(C)(C)C)C(=O)O)c(C)c(NS(C)(=O)=O)c3n1)N1CCC(C)(CC1)OCCCC[C@H](C)O2
Temperature: 100 °C
Reaction time: 24 h
Yield: 12.8 %

Procedure:
To a solution of methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (21 mg, 0.025 mmol, 1 equiv), methanesulfonamide (7 mg, 0.076 mmol, 3 equiv), CuI (7 mg, 0.038 mmol, 1.5 equiv), and K2CO3 (14 mg, 0.101 mmol, 4 equiv) in DMF (1.3 mL) was added (1S,2S)-(+)-N,N′-dimethylcyclohexanr-1,2-diamine (0.012 mL, 0.076 mmol, 3 equiv). The now blue reaction was heated to 100° C. for 24 h. More methanesulfonamide (7 mg, 0.076 mmol, 3 equiv), CuI (7 mg, 0.038 mmol, 1.5 equiv), and (1S,2S)-(+)-N,N′-dimethylcyclohexanr-1,2-diamine (0.012 mL, 0.076 mmol, 3 equiv) was added and the temperature was raised to 120° C. After 24 h, the reaction was removed from heat. Upon cooling to ambient temperature, the reaction was diluted with EtOAc and washed with water. The EtOAc was dried (Na2SO4) and concentrated in vacuo. The crude product was taken up in 9:1 MeOH:water (1 mL) and LiOH.H2O (32 mg, 0.759 mmol, 30 equiv) was added. The reaction was heated to 70° C. for 2 h. Upon cooling to ambient temperature, the reaction was filtered and purified via preparative LC/MS with the following conditions: The crude material was purified via preparative LC/MS with the following conditions: The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient: 50-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min to provide the product (2.4 mg, 12% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.16 (s, 1H), 8.08 (d, J=7.7 Hz, 1H), 8.04 (s, 1H), 7.54 (t, J=7.7 Hz, 1H), 7.35 (d, J=8.1 Hz, 1H), 7.15 (d, J=10.3 Hz, 1H), 7.10 (d, J=6.2 Hz, 1H), 6.00-5.82 (m, 1H), 4.63 (br. s., 1H), 3.89-3.80 (m, 1H), 3.70-3.59 (m, 1H), 3.52-3.42 (m, 5H), 3.37-3.19 (m, 1H), 2.72-2.64 (m, 1H), 2.41 (s, 3H), 2.29 (s, 3H), 1.97-1.50 (m, 10H), 1.22 (s, 3H), 1.18 (s, 9H), 1.08 (d, J=5.9 Hz, 3H); LCMS (ESI, M): 750.3.