Hydrochloric Acid → 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoic acid

HRID 1651019Notes

Reaction equation

HRID 1651019 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]([CH:27]([CH3:29])[CH3:28])[C:22]([O:24]CC)=[O:23])[O:13][C:12]1([CH3:31])[CH3:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.C(OCC)(=O)C.[OH-].[K+].Cl>C(O)C.O>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[C@H:14]([CH:20]=[C:21]([CH:27]([CH3:29])[CH3:28])[C:22]([OH:24])=[O:23])[O:13][C:12]1([CH3:31])[CH3:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexaneHCID 70045745ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate

Product 1

HCID 700456323-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

400 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate was dissolved in 0.2 ml of ethanol and 2.32 ml of an ethanol/water (10/1) solution of 2N potassium hydroxide was added thereto. The mixture was stirred at room temperature for 3 hours and further stirred for 1 hour at 55° C. 24 ml of water was added to the reaction solution, and the reaction solution was adjusted to pH 2 with 1N hydrochloric acid under cooling with ice. The solution was extracted three times with ethyl acetate, and the organic layer was washed with sequentially water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 375 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoic acid as a colorless oily substance.

Workup

  1. stirringfurther stirred for 1 hour at 55° C
  2. temperatureunder cooling with ice
  3. extractionThe solution was extracted three times with ethyl acetate
  4. washthe organic layer was washed with sequentially water
  5. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-50999fdb88624edbbb1c7c48ac3b3884
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

Loading…