C(OC([NH:11][CH2:12][CH2:13][N:14]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:15]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18])=O)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[C:28]([O:27][C:25]([N:14]1[C:15]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=2[C:17](=[O:18])[NH:11][CH2:12][CH2:13]1)=[O:26])([CH3:31])([CH3:30])[CH3:29]A solution of 2-[(2-benzyloxycarbonylaminoethyl)-tert-butoxycarbonylamino]-3-fluorobenzoic acid from Example 20B (390 mg, 0.87 mmol), 10% palladium/carbon (˜100 mg) and acetic acid (1.0 ml) in methanol (25 ml) was hydrogenated at atmospheric pressure for 1.5 h. The mixture was filtered, evaporated in vacuo and azeotroped with toluene. The residue was taken up in a mixture of IPA and acetic acid (90:10, 35 ml) and heated at reflux for 4 h. The mixture was cooled, evaporated in vacuo and azeotroped with toluene to give a white solid; yield 250 mg, 100%.
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