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

HRID 232139Notes

Reaction equation

HRID 232139 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.Cl.O>CCCCCC.C(OCC)(=O)C.[OH-].[K+]>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 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 acid

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

199 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate was dissolved in 1.16 ml of an ethanol/water (10/1) solution of 2N potassium hydroxide, and the mixture was stirred overnight at room temperature. The mixture was cooled to 0° C. and adjusted to pH 2 with 1N hydrochloric acid, and then 12 ml of water was added thereto. The mixture was extracted 3 times with 10 ml of ethyl acetate. The organic solvent layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoic acid as a colorless oily substance.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe mixture was extracted 3 times with 10 ml of ethyl acetate
  3. washThe organic solvent layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4cc681a804884a63a35daa9a2cef9ca8
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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