4-Benzyl 1,4-di-tert-butyl (1S)-6-[4-(benzyloxy)phenyl]-1-[(tert-butoxycarbonyl)amino]hexane-1,4,4-tricarboxylate → (5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[2-(4-hydroxyphenyl)ethyl]-6-oxohexanoic acid
Reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])([C:36]([O:38]CC2C=CC=CC=2)=[O:37])[CH2:18][CH2:19][C@H:20]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[C:24]([O:23][C:21](=[O:22])[C@@H:20]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:19][CH2:18][C:17]([C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])([CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[C:36]([OH:38])=[O:37])([CH3:25])([CH3:26])[CH3:27]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 125 mg of 4-benzyl 1,4-di-tert-butyl (1S)-6-[4-(benzyloxy)phenyl]-1-[(tert-butoxycarbonyl)amino]hexane-1,4,4-tricarboxylate (0.18 mmol) in methanol (5 mL) was added 10% palladium on charcoal (15 mg) and the mixture was stirred under an atmosphere of hydrogen for 16 h at room temperature. The catalyst was removed by filtration, and the filtrate was evaporated to give the target compound (84 mg, 89% yield) which was used without further purification.
Workup
- customThe catalyst was removed by filtration
- customthe filtrate was evaporated
Sources & evidence
- ORD record
- ord-8538f890aec44cc3aba7c975a0b828c7
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238631B2
Reaction notes
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