C(OC([NH:11][C@H:12]([CH2:30][CH2:31][CH2:32][NH:33]C(OCC1C=CC=CC=1)=O)[CH2:13][C:14]([NH:16][CH2:17][CH2:18][NH:19]C(OCC1C=CC=CC=1)=O)=[O:15])=O)C1C=CC=CC=1.[H][H]>CO.O.[C].[Pd]>[NH2:11][C@H:12]([CH2:30][CH2:31][CH2:32][NH2:33])[CH2:13][C:14]([NH:16][CH2:17][CH2:18][NH2:19])=[O:15]In 180 ml of methanol were suspended 1.41 g (2.39 mmol) of (R)-3,6-bis(benzyloxycarbonylamino)-N-(2-benzyloxycarbonylaminoethyl)hexanamide. To the resulting suspension was added a suspension of 718 mg of 10% palladium-carbon in 20 ml of water. After stirring, hydrogen gas was passed through the resulting mixture at room temperature for 3 hours to effect the reaction. The palladium-corbon was filtered off from the reaction mixture obtained, and the filtrate was concentrated to dryness. The residue obtained was dissolved in 15 ml of water and then subjected to a chromatography on a column of "Amberlite CG-50" (trade name, NH4+ -form, 50 ml). After the column was washed with 200 ml of water, the column was eluted with aqueous ammonia at concentrations gradiently varying from 0.5% to 4.0% (0.5%-increased steps; 200 ml at each concentration). Fractions of the eluate as eluted with 2.5% to 3.5% aqueous ammonia were combined together and concentrated to dryness, to afford 445 mg of (R)-3,6-diamino-N-(2-aminoethyl)hexanamide as a colorless paste.
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