di-tert-butyl (5S)-2-[4-(benzyloxy)benzyl]-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate → (5S)-2-(tert-Butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-(4-hydroxybenzyl)hexanedioic acid 6-tert-butyl ester
Reaction equation
C([O:8][C:9]1[CH:51]=[CH:50][C:12]([CH2:13][C:14]([C:40]([O:42]CC2C=CC=CC=2)=[O:41])([CH2:22][CH2:23][C@H:24]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[C:28]([O:27][C:25](=[O:26])[C@@H:24]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:23][CH2:22][C:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:51][CH:50]=1)[C:40]([OH:42])=[O:41])([CH3:29])([CH3:30])[CH3:31]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1.07 g di-tert-butyl (5S)-2-[4-(benzyloxy)benzyl]-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate (1.52 mmol) in methanol (20 mL) was added a 10% palladium on carbon hydrogenation catalyst (100 mg) at room temperature. The suspension was stirred overnight at room temperature under an atmosphere of hydrogen. The catalyst was removed by filtration and all volatiles were removed in vacuo. The crude product (800 mg, quantitative yield) was used in the next step without further purification.
Workup
- customThe catalyst was removed by filtration
- customall volatiles were removed in vacuo
Sources & evidence
- ORD record
- ord-abbc217e71944dce9221118731a1c1be
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238631B2
Reaction notes
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