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

HRID 1651017

Reaktionsgleichung

Reaktionsgleichung von HRID 1651017
[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]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 70040836ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoate

Produkt 1

HCID 571587953-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14797Potassium HydroxideLösungsmittelHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

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 mixture was stirred for 3 hours at room temperature. The reaction solution was adjusted to pH 2 with 1N hydrochloric acid under cooling with ice. Then, 24 ml of water was added thereto and extracted three times with 20 ml of ethyl acetate. The organic layer was washed sequentially with water and 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-2propenoic acid as a colorless oily substance.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. extractionextracted three times with 20 ml of ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-910163755a344ba6b81f914995f78ea5
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927565

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