Hydrochloric Acid → 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid

HRID 232130Notes

Reaction equation

HRID 232130 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][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[C:22]([O:24]CC)=[O:23])[O:13][C:12]1([CH3:37])[CH3:36])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>CCCCCC.C(OCC)(=O)C.[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][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[C:22]([OH:24])=[O:23])[O:13][C:12]1([CH3:37])[CH3:36])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 70045583ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate

Product 1

HCID 700453933-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

400 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate was dissolved in 1.93 ml of an ethanol/water (10/1) solution of 2N potassium hydroxide, and the solution was stirred overnight at room temperature. 24 ml of water was added thereto, and the mixture was cooled to 0° C., then neutralized with 1N hydrochloric acid and extracted three times with 15 ml of ethyl acetate. The ethyl acetate 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-5yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid as a colorless oily substance.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. extractionextracted three times with 15 ml of ethyl acetate
  3. washThe ethyl acetate 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-4475b190f4b04d49905197316e5bec46
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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