Reaction SMILES: [NH:1]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C@H:2]([C:11]([NH:13][C@H:14]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@H:28]([C:31]([NH:33]N)=[O:32])[CH2:29][OH:30])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[CH2:15][OH:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.N(OCCC(C)C)=O.[N-]=[N+]=[N-].N[C@H:57]([C:61]([NH:63][C@H:64]([C:69]([NH:71][C@H:72]([C:77]([NH:79][C@H:80]([C:86]([NH:88][C@H:89]([C:95]([NH:97][C@H:98]([C:101]([NH:103][C@H:104]([C:109]([NH:111][C@H:112]([C:120]([NH:122][C@H:123]([C:126]([NH:128][C@H:129]([C:145]([NH:147][C@H:148]([C:154]([OH:156])=[O:155])[CH2:149][CH2:150][C:151](=[O:153])[OH:152])=[O:146])[CH2:130][CH2:131][CH2:132][CH2:133][NH:134][S:135]([C:138]1[CH:144]=[CH:143][C:141]([CH3:142])=[CH:140][CH:139]=1)(=[O:137])=[O:136])=[O:127])[CH2:124][OH:125])=[O:121])[CH2:113][CH2:114][CH2:115][NH:116][C:117](=[NH:119])[NH2:118])=[O:110])[CH2:105][CH:106]([CH3:108])[CH3:107])=[O:102])[CH2:99][OH:100])=[O:96])[CH2:90][CH2:91][C:92](=[O:94])[OH:93])=[O:87])[CH2:81][CH2:82][C:83](=[O:85])[NH2:84])=[O:78])[CH2:73][CH:74]([CH3:76])[CH3:75])=[O:70])[CH2:65][C:66](=[O:68])[NH2:67])=[O:62])[C@@H:58]([CH3:60])[OH:59]>CN(C)C=O.NN.C(N(CC)CC)C.O1CCOCC1>[NH:1]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C@H:2]([C:11]([NH:13][C@H:14]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@H:28]([C:31]([NH:33][C@H:57]([C:61]([NH:63][C@H:64]([C:69]([NH:71][C@H:72]([C:77]([NH:79][C@H:80]([C:86]([NH:88][C@H:89]([C:95]([NH:97][C@H:98]([C:101]([NH:103][C@H:104]([C:109]([NH:111][C@H:112]([C:120]([NH:122][C@H:123]([C:126]([NH:128][C@H:129]([C:145]([NH:147][C@H:148]([C:154]([OH:156])=[O:155])[CH2:149][CH2:150][C:151](=[O:152])[OH:153])=[O:146])[CH2:130][CH2:131][CH2:132][CH2:133][NH:134][S:135]([C:138]1[CH:144]=[CH:143][C:141]([CH3:142])=[CH:140][CH:139]=1)(=[O:137])=[O:136])=[O:127])[CH2:124][OH:125])=[O:121])[CH2:113][CH2:114][CH2:115][NH:116][C:117](=[NH:118])[NH2:119])=[O:110])[CH2:105][CH:106]([CH3:107])[CH3:108])=[O:102])[CH2:99][OH:100])=[O:96])[CH2:90][CH2:91][C:92](=[O:93])[OH:94])=[O:87])[CH2:81][CH2:82][C:83](=[O:85])[NH2:84])=[O:78])[CH2:73][CH:74]([CH3:76])[CH3:75])=[O:70])[CH2:65][C:66](=[O:68])[NH2:67])=[O:62])[C@@H:58]([CH3:60])[OH:59])=[O:32])[CH2:29][OH:30])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[CH2:15][OH:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1
Reactant: CC(C)C[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1)C(=O)N[C@@H](CO)C(=O)NN
Reactant: Cc1ccc(S(=O)(=O)NCCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](N)[C@@H](C)O)C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
Agent: CC(C)CCON=O
Agent: NN
Agent: [N-]=[N+]=[N-]
Solvent: C1COCCO1
Solvent: CN(C)C=O
Solvent: CCN(CC)CC
Product: Cc1ccc(S(=O)(=O)NCCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)OCc2ccccc2)[C@@H](C)O)C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
Temperature: -15 °C

Procedure:
42.3 Milligrams of Z-Tyr-Ser-Leu-Ser-NHNH2 was dissolved in 4 ml of dimethylformamide, further 0.34 ml of 10-hold diluted-dimethylformamide solution of 6 NOhydrochloric acid/dioxane was added thereto, and the mixture was cooled to -15° C., then 0.091 ml of 10-hold diluted-dimethylformamide solution of isoamyl nitrite was added with stirring. After the reaction mixture shows a negative reaction in hydrazine-test, 0.29 ml of 10-hold diluted-dimethylformamide solution of triethylamine was added drop by drop in small amounts to neutralize the reaction mixture. This reaction mixture containing azide product was added to 4 ml of a cold dimethylformamide solution containing 50.0 mg of H-Thr-Asn-Leu-Gln-Glu-Ser-Leu-Arg-Ser-Lys(Tos)-Glu-OH and 0.1 ml of 10-fold diluted-dimethylformamide solution of triethylamine, then the whole mixture was stirred at -10° to -15° C. for 2 hours, next at 4° C. for 18 hours. Further, a product being converted 42.3 mg of Z-Tyr-Ser-Leu-Ser-NHNH2 into an azide was added thereto and was reacted for 24 hours. Dimethylformamide was removed by distillation under a reduced pressure, the residue obtained was extracted with 30 ml of n-butanol being saturated with water, the extract was washed 10 times with water being saturated with n-butanol, next washed 5 times with 2%-acetic acid being saturated with n-butanol. The organic layers were collected and subjected to distillation under a reduced pressure to remove n-butanol, then the residue was lyophilized, reprecipitated from ethyl acetate-ether to obtain the desired product.