Hydrochloric Acid → Hydrochloric Acid
Reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:4][CH:3]1[C:5]([NH:7][C:8](=[CH:16][CH2:17][CH2:18][CH3:19])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:6].[ClH:21].C[CH2:23][O:24]CC>>[CH3:1][C:2]1([CH3:20])[CH2:4][CH:3]1[C:5]([NH:7][C:8]([O:24][CH3:23])([CH:16]=[CH:17][CH2:18][CH3:19])[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[O:6].[ClH:21]Participants
Procedure
A solution of 0.84 g (3.0 mmole) of t-butyl 2-(2,2-dimethylcyclopropanecarboxamido)-2-hexenoate in 10 ml of Et2O saturated with anhydrous HCl was allowed to stand at room temperature under a drying tube. After 17 hrs, the solution was evaporated, and the residual gum was dissolved in 10 ml of saturated NaHCO3. This solution was washed with an additional 15 ml of 0.5 N HCl, then dried (MgSO4), filtered, and concentrated to give a viscous oil. The oil was crystallized from toluene. Yield of white crystals =0.32 g (47%), m.p. 119°-122°. TLC (4:1 toluene-AcOH) showed a single spot. NMR indicated essentially pure Z-isomer. (Note: Treatment of the methanol adduct, t-butyl 2-(2,2-dimethylcyclopropanecarboxamido)-2-methoxyhexenoate, with anhydrous HCl in Et2O under similar conditions gave the same product.)
Workup
- customto stand at room temperature under a drying tube
- customthe solution was evaporated
- dissolutionthe residual gum was dissolved in 10 ml of saturated NaHCO3
- washThis solution was washed with an additional 15 ml of 0.5 N HCl
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto give a viscous oil
- customThe oil was crystallized from toluene
Sources & evidence
- ORD record
- ord-0a9619c08e414c50bf6a64d4674ec042
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05147868
Reaction notes
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