O.[OH-].[Li+].C[O:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH:10]([CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][N:8]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[C:25]([O:24][C:22]([N:8]1[CH2:9][CH:10]([CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:7]1[C:6]([OH:29])=[O:5])=[O:23])([CH3:27])([CH3:28])[CH3:26]Lithium hydroxide monohydrate (7 mg) was added to a solution of N-tert-butoxycarbonyl-4-[2-(tert-butoxycarbonylamino)ethyl]-L-proline methyl ester (E, 50 mg) in tetrahydrofuran (0.5 mL)-methanol (0.5 mL)-water (0.5 mL). After stirring at room temperature for 4 hr, the reaction mixture was acidified with 10% citric acid and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give the title compound (52 mg).
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