C([O:8][C:9](=[O:41])[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:40])[C:18]([CH3:39])([CH3:38])[CH:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:20][C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]([C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>CO.[OH-].[Pd+2].[OH-]>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:21]([NH:20][CH:19]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:18]([CH3:39])([CH3:38])[C:17]([N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][C:9]([OH:41])=[O:8])[CH2:16][CH2:15]2)=[O:40])=[O:31])=[CH:27][CH:26]=1)(=[NH:29])[NH2:30]N-4-Amidinobenzoyl-β-phenyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid benzyl ester (63 mg, 0.114 mmol) was dissolved in an 80% aqueous methanol solution (10 ml) containing 2% acetic acid. To the reulting solution was added palladium hydroxide (50 mg) and the mixture was stirred in a hydrogen atmosphere for 15 minutes. The solvents were distilled off and the res idue was dissolved in a 1N aqueous solution of acetic acid. The resulting solution was purified with a high performance liquid chromatography (HPLC) under the same conditions as described in (3) to yield a powder of N-(N-4-amidinobenzoyl-β-phenyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid (47.5 mg, 89.9%). The obtained product was identified by NMR, MS and HPLC analyses to be the same compound as prepared by the solid phase method.
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