(5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acid → Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(5-hydroxypyridin-2-yl)methyl]hexanedioate
Reaction equation
[C:1]([O:5][C:6](=[O:37])[C@@H:7]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:8][CH2:9][C:10]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][N:16]=1)C(O)=O)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:33]([O:32][C:30]([NH:29][C@@H:7]([CH2:8][CH2:9][CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][N:16]=1)[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:37])=[O:31])([CH3:34])([CH3:35])[CH3:36]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 220 mg of (5S)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acid (0.42 mmol) and 100 mg 4-N,N-dimethylaminopyridine (0.84 mmol) in 1,4-dioxan (10 mL) was heated under reflux for 2 hours. The mixture was evaporated and the residue was purified by column preparative HPLC (method C) to give two batches (107+49 mg; 78% combined yield) of the target compound.
Workup
- temperatureunder reflux for 2 hours
- customThe mixture was evaporated
- customthe residue was purified by column preparative HPLC (method C)
- customto give
- customtwo batches (107+49 mg; 78% combined yield) of the target compound
Sources & evidence
- ORD record
- ord-a3a980d9369447adab609c1e1b9ea7f7
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238631B2
Reaction notes
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