Reaction SMILES: C1(OC)C=CC=CC=1.[NH:9](C(OCC1C=CC=CC=1)=O)[C@H:10]([C:28]([NH:30][C@H:31]([C:36]([NH:38][C@H:39]([C:44]([NH:46][C@H:47]([C:53]([NH:55][CH2:56][C:57]([NH:59][C@H:60]([C:65]([NH:67][C@H:68]([C:72]([NH2:74])=[O:73])[CH:69]([CH3:71])[CH3:70])=[O:66])[CH2:61][CH:62]([CH3:64])[CH3:63])=[O:58])=[O:54])[CH2:48][CH2:49][C:50](=[O:52])[NH2:51])=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:32][CH:33]([CH3:35])[CH3:34])=[O:29])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:27])[NH:16][S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].CN1CCOCC1.[NH:92]([C:109]([O:111][CH2:112][C:113]1[CH:118]=[CH:117][CH:116]=[CH:115][CH:114]=1)=[O:110])[C@H:93]([C:99]([O:101]N1C(=O)CCC1=O)=O)[CH2:94][CH2:95][C:96](=[O:98])[NH2:97].Cl>C(O)(=O)C.CN(C)C=O.CCOCC>[NH:92]([C:109]([O:111][CH2:112][C:113]1[CH:114]=[CH:115][CH:116]=[CH:117][CH:118]=1)=[O:110])[C@H:93]([C:99]([NH:9][C@H:10]([C:28]([NH:30][C@H:31]([C:36]([NH:38][C@H:39]([C:44]([NH:46][C@H:47]([C:53]([NH:55][CH2:56][C:57]([NH:59][C@H:60]([C:65]([NH:67][C@H:68]([C:72]([NH2:74])=[O:73])[CH:69]([CH3:71])[CH3:70])=[O:66])[CH2:61][CH:62]([CH3:63])[CH3:64])=[O:58])=[O:54])[CH2:48][CH2:49][C:50](=[O:52])[NH2:51])=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:32][CH:33]([CH3:35])[CH3:34])=[O:29])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:27])[NH:16][S:17]([C:20]1[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=1)(=[O:19])=[O:18])=[O:101])[CH2:94][CH2:95][C:96](=[O:98])[NH2:97]
Reactant: NC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)ON1C(=O)CCC1=O
Reactant: Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)OCc2ccccc2)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(N)=O)C(C)C)cc1
Agent: Cl
Solvent: CCOCC
Solvent: CN1CCOCC1
Solvent: CN(C)C=O
Product: Cc1ccc(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)OCc2ccccc2)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(N)=O)C(C)C)cc1
Temperature: 25 °C
Reaction time: 1.5 h
Yield: 84 %

Procedure:
In a mixed liquid of 100 ml of acetic acid, 100 ml of 25% HBR-acetic acid and 3.4 g of anisole is dissolved 33.5 g (30.9 millimoles) of Z-Arg(Tos)-Leu-Leu-Gln-Gly-Leu-Val-NH2, and the solution is stirred at room temperature for 1.5 hours and is then added to 2.5 l of ether. The formed precipitate is recovered by decantation and dissolved in 300 ml of ethanol. The solution is added to ether and an HBr salt of the Z-compound is recovered by decantation. Then, the recovered salt (34.5 g, 30.9 millimoles) is dissolved in 400 ml of dimethylformamide, and 6.8 g of N-methylmorpholine is added to the solution under cooling. Then, 14 g (37 millimoles) of crystalline Z-Gln-OSu is added to the mixture, and the mixture is stirred at -5° C. for 2 hours and allowed to stand at room temperature for 2 days. Then, 2 g of N-(2-aminoethylpiperazine) is added to the reaction mixture, and the mixture is stirred for 30 minutes and added to 2.5 l of 1 N HCl. The formed precipitate is recovered by filtration, washed with water, suspended in 400 ml of methanol, stirred and recovered by filtration to obtain 31.5 g of intended Z-Gln-Arg(Tos)-Leu-Leu-Gln-Gly-Leu-Val-NH2 (the yield being 84.2%).