Reaction SMILES: CC(O[C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:23]([OH:25])=[O:24])=[O:7])(C)C.[NH2:26][C:27]1[CH:38]=[CH:37][C:30]([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])=[CH:29][CH:28]=1.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[C:44](/[CH:46]=[CH:47]/[C:48]([OH:50])=O)[CH:45]=1.CN1C(=O)CC(=O)N(C)C1=O>CN(C)C=O.C(OC(C)C)(C)C.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[C:44](/[CH:46]=[CH:47]/[C:6]([N:8]2[CH2:12][C@@H:11]([CH:13]3[CH2:14][CH2:15][N:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:17][CH2:18]3)[CH2:10][C@H:9]2[C:23]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])=[CH:37][CH:38]=2)=[O:25])=[O:7])[CH:45]=1.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([N:51]2[CH:55]=[N:54][N:53]=[N:52]2)=[C:44](/[CH:46]=[CH:47]/[C:48]([N:8]2[CH2:12][C@@H:11]([CH:13]3[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]3)[CH2:10][C@H:9]2[C:23]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:37][CH:38]=2)=[O:24])=[O:50])[CH:45]=1
Reactant: O=C(O)/C=C/c1cc(Cl)ccc1-n1cnnn1
Reactant: CC(C)(C)OC(=O)N1C[C@@H](C2CCN(S(C)(=O)=O)CC2)C[C@H]1C(=O)O
Reactant: C=CCOC(=O)c1ccc(N)cc1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: CN1C(=O)CC(=O)N(C)C1=O
Solvent: ClCCl
Solvent: CN(C)C=O
Solvent: CC(C)OC(C)C
Product: C=CCOC(=O)c1ccc(NC(=O)[C@@H]2C[C@H](C3CCN(S(C)(=O)=O)CC3)CN2C(=O)/C=C/c2cc(Cl)ccc2-n2cnnn2)cc1
Product: CS(=O)(=O)N1CCC([C@H]2C[C@@H](C(=O)Nc3ccc(C(=O)O)cc3)N(C(=O)/C=C/c3cc(Cl)ccc3-n3cnnn3)C2)CC1
Temperature: 25 °C
Reaction time: 8 h

Procedure:
Allyl 4-[({(2S,4R)-1-{(2E)-3-[5-chloro-2-(1H-tetrazol-1-yl)phenyl]-2-propenoyl}-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinyl}carbonyl)amino]benzoate was prepared by following the procedures described in Examples 5, 9 and 8 starting from the compound prepared in Example 63. (Note: in the step corresponding to Example 5, allyl 4-aminobenzoate was used in place of tert-butyl 4-aminobenzoate. In the step corresponding to Example 8, (2E)-3-[5-chloro-2-(1H-tetrazol-1-yl)phenyl]acrylic acid was used in place of 1-(N,N′-bis(tert-butoxycarbonyl)carbamimidoyl)piperidine-4-carboxylic acid). After that, to a solution of the crude allyl ester (48 mg) in N,N-dimethylformamide (1 mL) was added tetrakis(triphenylphosphine)palladium(0) (2 mg) and 1,3-dimethylbarbituric acid (4 mg) and the reaction stirred overnight at room temperature. Further tetrakis(triphenylphosphine)palladium(0) (3 mg) was added at this juncture and stirring continued at room temperature for 7 h. The reaction mixture was left to stand overnight, diluted with a 1:1 mixture of diisopropylether and dichloromethane (1 mL) and the resulting precipitate collected by filtration. The yellow powder obtained was washed with dichloromethane and dried to give the title compound having the following physical properties (25 mg).