Reaction SMILES: [NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:24]([N:26]1[CH2:120][CH2:119][CH2:118][C@H:27]1[C:28]([NH:30][C@H:31]([C:42]([NH:44][C@H:45]([C:56]([N:58]1[CH2:117][CH2:116][CH2:115][C@H:59]1[C:60]([NH:62][C@H:63]([C:74]([NH:76][C@H:77]([C:85]([NH:87][C@H:88]([C:96]([NH:98][C@H:99]([C:112]([NH2:114])=[O:113])[CH2:100][CH2:101][CH2:102][CH2:103][NH:104][C:105]([O:107][C:108]([CH3:111])([CH3:110])[CH3:109])=[O:106])=[O:97])[CH2:89][CH2:90][CH2:91][NH:92][C:93](=[NH:95])[NH2:94])=[O:86])[CH2:78][CH2:79][CH2:80][NH:81][C:82](=[NH:84])[NH2:83])=[O:75])[CH2:64][C:65]1[C:73]2[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=2)[NH:67][CH:66]=1)=[O:61])=[O:57])[CH2:46][C:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:49][CH:48]=1)=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1)=[O:29])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]>CO>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:24]([N:26]1[CH2:120][CH2:119][CH2:118][C@H:27]1[C:28]([NH:30][C@H:31]([C:42]([NH:44][C@H:45]([C:56]([N:58]1[CH2:117][CH2:116][CH2:115][C@H:59]1[C:60]([NH:62][C@H:63]([C:74]([NH:76][C@H:77]([C:85]([NH:87][C@H:88]([C:96]([NH:98][C@H:99]([C:112]([NH2:114])=[O:113])[CH2:100][CH2:101][CH2:102][CH2:103][NH:104][C:105]([O:107][C:108]([CH3:111])([CH3:110])[CH3:109])=[O:106])=[O:97])[CH2:89][CH2:90][CH2:91][NH:92][C:93](=[NH:94])[NH2:95])=[O:86])[CH2:78][CH2:79][CH2:80][NH:81][C:82](=[NH:83])[NH2:84])=[O:75])[CH2:64][C:65]1[C:73]2[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=2)[NH:67][CH:66]=1)=[O:61])=[O:57])[CH2:46][C:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:49][CH:48]=1)=[O:43])[CH2:32][C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1)=[O:29])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]
Reactant: CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc1ccccc1)C(N)=O
Solvent: CO
Product: CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](N)CCCNC(=N)N)C(N)=O

Procedure:
A methanol solution of 1.00 equivalent of 3TPB.Z-Arg-Trp-Pro-TrpTrp-Pro-Trp-Arg-Arg-Lys(Boc)-NH2 (Mw=1787.1; purity=57.0%;) was passed several times through a column containing a methanol washed resin IRA 958 (Mw=1000, 9.00 equivalents). After the exchange had been checked by HPLC, the resin was filtered and washed three times with methanol. The combined organic phases were partially concentrated in vacuo. The concentrated solution was then diluted with water and Pd catalyst was added. The suspension was then hydrogenated for at least 6 hours at 35±5° C. The catalyst was filtered off, washed three times with a mixture methanol/water. The combined filtrates were evaporated in vacuo, the residue suspended in DMA and further concentrated in order to eliminate the remaining water. After checking the water content, the solution was titrated by HCl (0.1N) or NMR and further used without any purification.