Reaction SMILES: Cl.[CH:2]1[C:14]2[CH:13]([CH2:15][O:16][C:17]([NH:19][C@@H:20]([CH2:25]I)[C:21]([O:23][CH3:24])=[O:22])=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38](I)=[C:37]([F:42])[CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C=O)C.[Zn].II.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(OCC)(=O)C>[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:25][C@H:20]([NH:19][C:17]([O:16][CH2:15][CH:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:6]3[C:14]2=[CH:2][CH:3]=[CH:4][CH:5]=3)=[O:18])[C:21]([O:23][CH3:24])=[O:22])=[C:37]([F:42])[CH:36]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
Reactant: Fc1cc(OCc2ccccc2)ccc1I
Reactant: COC(=O)[C@H](CI)NC(=O)OCC1c2ccccc2-c2ccccc21
Agent: COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1
Agent: Cl
Agent: II
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Solvent: O
Product: COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1F)NC(=O)OCC1c2ccccc2-c2ccccc21
Yield: 76.5 %

Procedure:
A zinc powder (51.6 g, 789 mmol) was added to 1 N hydrochloric acid (100 mL), the resultant mixture was sonicated and then allowed to stand, and then a supernatant was removed therefrom. This procedure was repeated two times. Water (300 mL) was added to the resultant zinc residue, the resultant solution was stirred and then allowed to stand, and then a supernatant was removed therefrom. This procedure was repeated three times. Acetone (300 mL) was added to the resultant product, the mixture was stirred and then allowed to stand, a supernatant was removed therefrom, then diethyl ether (300 mL) was added to the solution, the resultant solution was stirred and then allowed to stand, a supernatant was removed therefrom, and a residue was then dried under reduced pressure to give activated zinc. To the activated zinc were added DMF (120 mL) and iodine (3.36 g, 13.2 mmol) under a nitrogen atmosphere at room temperature. The resultant mixture was stirred at room temperature for 45 minutes. To the reaction mixture was added a solution of methyl(2R)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-3-iodopropanoate (120 g, 266 mmol) described in Production Example 1-2-3 in DMF (500 mL) over 30 minutes under a nitrogen atmosphere at room temperature. The resultant mixture was stirred at room temperature for 40 minutes. To the reaction mixture were added 4-(benzyloxy)-2-fluoro-1-iodobenzene (104 g 318 mmol) described in Production Example 1-2-5, tris(dibenzylideneacetone)palladium (0) (6.00 g, 6.55 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (5.40 g, 13.2 mmol) under a nitrogen atmosphere at room temperature. The resultant mixture was stirred at room temperature for 20 hours and 40 minutes. Water and ethyl acetate were added to the reaction mixture, and the resultant solution was filtrated using Celite. A filtrate was partitioned, and an aqueous layer was further extracted with ethyl acetate three times. A combined organic layer was washed with water and saturated brine. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, then diethyl ether (1.00 L) and heptane (1.00 L) were added to the resultant residue, and then a precipitate was collected by filtration. Diethyl ether (500 mL) and heptane (500 mL) were added to the filtrated solid, and a precipitate was collected by filtration to give the title compound (107 g, yield: 77%).