Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH:20]=[C:21]([CH2:27][CH3:28])[C:22]([O:24]CC)=[O:23])[O:13][C:12]1([CH3:30])[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C(O)C.O.[OH-].[K+]>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH:20]=[C:21]([CH2:27][CH3:28])[C:22]([OH:24])=[O:23])[O:13][C:12]1([CH3:30])[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
517 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoate was dissolved in 3.10 ml of an ethanol/water (9/1) solution of 2N potassium hydroxide, and the solution was stirred at room temperature for 3 hours. Then, the reaction solution was adjusted to pH2 with 1N hydrochloric acid under cooling with ice and after an addition of 24 ml of water, extracted three times with 20 ml of ethyl acetate. The organic layer was washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoic acid as colorless oily substance.
Workup
- temperatureunder cooling with ice
- extractionextracted three times with 20 ml of ethyl acetate
- washThe organic layer was washed with water and with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-b9c56b21578a40928e47793a0d389286
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05122523
Linked notes
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