Reaction SMILES: [NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:44]([NH:46][C@H:47]([C:57]([NH:59][C@H:60]([C:64]([NH:66][C@H:67]([C:71]([NH:73][C@H:74]([C:84]([NH:86][C@H:87]([C:97]([NH:99][C@H:100]([C:102]([NH:104][C@H:105]([C:115]([NH:117][C@H:118]([C:123]([O:125][C:126]([CH3:129])([CH3:128])[CH3:127])=[O:124])[CH2:119][C:120](=[O:122])[NH2:121])=[O:116])[CH2:106][CH2:107][C:108](=[O:114])[O:109][C:110]([CH3:113])([CH3:112])[CH3:111])=[O:103])[CH3:101])=[O:98])[CH2:88][CH2:89][C:90](=[O:96])[O:91][C:92]([CH3:95])([CH3:94])[CH3:93])=[O:85])[CH2:75][CH2:76][C:77](=[O:83])[O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:72])[CH:68]([CH3:70])[CH3:69])=[O:65])[CH:61]([CH3:63])[CH3:62])=[O:58])[CH2:48][CH2:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]>[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:44]([NH:46][C@H:47]([C:57]([NH:59][C@H:60]([C:64]([NH:66][C@H:67]([C:71]([NH:73][C@H:74]([C:84]([NH:86][C@H:87]([C:97]([NH:99][C@H:100]([C:102]([NH:104][C@H:105]([C:115]([NH:117][C@H:118]([C:123]([O:125][C:126]([CH3:127])([CH3:128])[CH3:129])=[O:124])[CH2:119][C:120](=[O:122])[NH2:121])=[O:116])[CH2:106][CH2:107][C:108](=[O:114])[O:109][C:110]([CH3:113])([CH3:112])[CH3:111])=[O:103])[CH3:101])=[O:98])[CH2:88][CH2:89][C:90](=[O:96])[O:91][C:92]([CH3:93])([CH3:94])[CH3:95])=[O:85])[CH2:75][CH2:76][C:77](=[O:83])[O:78][C:79]([CH3:80])([CH3:81])[CH3:82])=[O:72])[CH:68]([CH3:70])[CH3:69])=[O:65])[CH:61]([CH3:63])[CH3:62])=[O:58])[CH2:48][CH2:49][C:50](=[O:56])[O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]
Reactant: CC(C)[C@H](NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OCc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)OC(C)(C)C)C(C)C
Agent: [Pd]
Agent: O=S(=O)([O-])[O-]
Agent: [Ba+2]
Product: CC(C)[C@H](NC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)[C@@H](N)CCC(=O)OC(C)(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)OC(C)(C)C)C(C)C
Reaction time: 3 h

Procedure:
A solution of Z-Glu(OtBu)-Lys(Boc)-Lys(Boc)-Glu(OtBu)-Val-Val-Glu(OtBu)-Glu(OtBu)-Ala-Glu(OtBu)-Asn-OtBu (45.0 g, 23 mmol) in TFE (1.1 L) containing 10% Pd-BaSO4 (15 g) was hydrogenated in a Vibromixer apparatus for 3 h. The reaction mixture was filtered through celite which was washed with TFE (3×100 mL). The combined filtrate was evaporated to dryness and taken up in DMF:DMSO (1300 mL:650 mL) for use in the next stage of synthesis. A portion of the residue was precipitated from TFE-H2O, filtered and dried in vacuo; mp 326°-327°; [α]D25 -17.65° (c 1, DMSO); Rf 0.73 (n-BuOH:AcOH:EtOAc:H2O; 1-1-1-1). Anal calc. for C88H154N14O27.H2O (1876.27): C, 56.33; H, 8.49; N, 10.45. Found: C, 56.40; H, 8.69; N, 10.55.