C(OC(=O)[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:78])[CH2:15][C@@H:16]([NH:67]C(OCC1C=CC=CC=1)=O)[CH2:17][CH2:18][CH2:19][NH:20][C:21]([C@H:23]1[NH:41][C:40](=[O:42])[C@H:39]([CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[NH:38][C:37](=[O:54])[C@@H:36]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:35][C:34]2[CH:63]=[C:30]([CH:31]=[CH:32][C:33]=2[OH:64])[C:29]2=[CH:65][C:25](=[C:26]([OH:66])[CH:27]=[CH:28]2)[CH2:24]1)=[O:22])C1C=CC=CC=1>[Pd].C(O)(=O)C.O.C(O)C>[C:50]([O:49][C:47](=[O:48])[NH:46][CH2:45][CH2:44][CH2:43][C@@H:39]1[NH:38][C:37](=[O:54])[C@@H:36]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:35][C:34]2[CH:63]=[C:30]([CH:31]=[CH:32][C:33]=2[OH:64])[C:29]2=[CH:65][C:25](=[C:26]([OH:66])[CH:27]=[CH:28]2)[CH2:24][C@@H:23]([C:21]([NH:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH2:67])[CH2:15][C:14]([NH:13][CH2:12][CH2:11][NH2:10])=[O:78])=[O:22])[NH:41][C:40]1=[O:42])([CH3:51])([CH3:52])[CH3:53]12 mg (0.011 mmol) of benzyl(2-{[(3S)-3-{[(benzyloxy)carbonyl]amino}-6-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-8-yl]carbonyl}amino)hexanoyl]amino}ethyl)carbamate (Example 190A) are added into 3 ml of a 4:1:1 acetic acid/water/ethanol mixture. 1.5 mg of palladium on activated carbon (10%) are added thereto, and the mixture is then hydrogenated at RT under atmospheric pressure for 15 h. The reaction mixture is filtered through prewashed kieselguhr and washed with ethanol, and the filtrate is concentrated on a rotary evaporator in vacuo.
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