(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester → (R)-2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid
Reaction equation
C([O:8][C:9](=[O:25])[C@@H:10]([NH:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>C1COCC1.[Pd]>[N:18]1([C:16]([NH:15][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:25])=[O:8])=[O:17])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1Participants
4
Procedure
A solution of (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester (38.5 g, 111 mmol) in 600 mL of THF was hydrogenated at 50 psi over 20% Pd/C (2.00 g) for 17 minutes. The reaction mixture was filtered through celite and concentrated to dryness. The residue was heated in 50 mL of hexane. The resulting suspension was cooled, and the solid was collected by filtration and washed with hexane. The solid was dried at room temperature under vacuum to give (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid as a white solid (26.6 g, 93%); mp 88-89° C.