Lithium Hydroxide → 6-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:13][C:9]2([CH2:12][CH2:11][CH2:10]2)[O:8][N:7]1[C:14](=[O:24])[CH:15]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]([CH3:18])[CH3:17])=[O:5])C.[OH-].[Li+]>C(O)C>[CH3:23][O:22][C:20]([NH:19][CH:15]([CH:16]([CH3:18])[CH3:17])[C:14]([N:7]1[CH:6]([C:4]([OH:5])=[O:3])[CH2:13][C:9]2([CH2:12][CH2:11][CH2:10]2)[O:8]1)=[O:24])=[O:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-(2-methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid ethyl ester (1.31 g, 3.83 mmol) in ethanol (10 mL) was added a solution of lithium hydroxide (1M in water, 7.6 mL, 7.6 mmol). The reaction was stirred at room temperature for 30 minutes. The reaction was partially concentrated and the resulting aqueous solution was washed with ethyl acetate. The ethyl acetate layer was discarded and the aqueous layer was acidified using concentrated HCl. The acidic aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to yield crude 6-(2-methoxycarbonylamino-3-methyl-butyryl)-5-oxa-6-aza-spiro[3.4]octane-7-carboxylic acid, which was used without further purification.
Workup
- concentrationThe reaction was partially concentrated
- washthe resulting aqueous solution was washed with ethyl acetate
- extractionThe acidic aqueous layer was extracted twice with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6b434d53795a48bb8f35dde9f0320aa6
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575118B2
Reaction notes
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