Lithium Hydroxide → HCID 178454206, compound
Reaction equation
C[O:2][C:3](=[O:25])[C:4]([NH:21][C:22]([NH2:24])=[NH:23])([OH:20])[C@@H:5]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:7][CH2:8][N+:9]([O-:11])=[O:10].[OH-].[Li+]>CO.O>[N+:9]([CH2:8][CH2:7][CH2:6][C@H:5]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:4]([NH:21][C:22]([NH2:24])=[NH:23])([OH:20])[C:3]([OH:25])=[O:2])([O-:11])=[O:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of the compound of Example 3 (5.0 g, 13.8 mmole) in 100 mL of methanol was treated with 17 mL of 1M lithium hydroxide. This solution was allowed to stir overnight and then treated with 20 mL of Dowex-50 resin X8 400 (H+ form) in 50 mL of deionized water. This solution was swirled for 15 minutes then passed through a 4×4 cm. column of the same resin, the column was washed with 1:1 methanol:water and the combined filtrates were concentrated to dryness under vacuum. The residue was dissolved in 100 mL acetonitrile and concentrated to dryness, this process was repeated two more times to give 4.2 g (87 % yield) of the above-identified compound as an off-white foam. 1H NMR (CD3OD) d 1.42 and 1.42 (s, 9H), 1.7 (m, 4H), 3.3 (m, 2H), 3.95 (m, 1H), 4.19 (bs, 0.65H), 4.33 (bs, 0.35H), 4.15 (d, J=1 Hz, 0.65H), 4.38 (d, J=4 Hz).
Workup
- waitThis solution was swirled for 15 minutes
- washcolumn of the same resin, the column was washed with 1:1 methanol
- concentrationwater and the combined filtrates were concentrated to dryness under vacuum
- dissolutionThe residue was dissolved in 100 mL acetonitrile
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-da2372cd3ba6409bb6158b0979d993ec
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05597804
Reaction notes
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