Lithium Hydroxide → 181645-94-3
Reaction equation
C([O:3][C:4](=[O:18])/[CH:5]=[CH:6]/[C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([CH3:9])[CH3:8])C.[OH-].[Li+].C(OCC)(=O)C>O1CCOCC1.O>[C:14]([O:13][C:11]([NH:10][C:7]([CH3:9])([CH3:8])/[CH:6]=[CH:5]/[C:4]([OH:18])=[O:3])=[O:12])([CH3:17])([CH3:15])[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
(2E)-4-tert-Butoxycarbonylamino-4-methylpent-2-enoic acid ethyl ester (5.0 g, 19.4 mmol) was dissolved in dioxane (50 ml). A solution of lithium hydroxide (0.61 g, 25.3 mmol) in water (25 ml) was added. The solution was stirred for 16 h at 20° C. Ethyl acetate (75 ml) and water (20 ml) were added. The phases were seperated, and the aqueous phase was extracted with ethyl acetate (20 ml). The combined organic phases were extracted with 1N sodium hydroxide solution (30 ml). The combined aqueous phases were acidified with iN sodium hydrogensulfate solution until pH=2. The aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were dried (magnesium sulfate) and the solvent removed in vacuo. The crude (2E)-4-tert-butoxycarbonylamino-4-methylpent-2-enoic acid was used for further syntheses.
Workup
- customThe phases were seperated
- extractionthe aqueous phase was extracted with ethyl acetate (20 ml)
- extractionThe combined organic phases were extracted with 1N sodium hydroxide solution (30 ml)
- extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
- dry with materialThe combined organic phases were dried (magnesium sulfate)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-e8d40a7c2f3b4525b4706a98e8629503
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350767B1
Reaction notes
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