Hydrochloric Acid → (+/-)-3-(2-Benzyloxy-5-iodophenyl)-2-tert-butoxycarbonylaminopropionic acid

HRID 269597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269597
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:12]=1[CH2:13][C:14]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(C(OCC)=O)[C:15]([O:17]CC)=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)C.Cl>O>[CH2:3]([O:10][C:11]1[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:12]=1[CH2:13][CH:14]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:15]([OH:17])=[O:16])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 66879924Diethyl 2-(2-benzyloxy-5-iodobenzyl)-2-tert-butoxycarbonylaminomalonate

Produkt 1

HCID 66879582(+/-)-3-(2-Benzyloxy-5-iodophenyl)-2-tert-butoxycarbonylaminopropionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

400 ml of a 1N sodium hydroxide solution are added to a suspension of 58 g (97 mmol) of diethyl 2-(2-benzyloxy-5-iodobenzyl)-2-tert-butoxycarbonylaminomalonate (Example 5A) in 800 ml of a mixture of ethanol and water (7:3). After 3 h under reflux and after cooling to room temperature, the pH of the reaction mixture is adjusted to about pH 2 with conc. hydrochloric acid. The reaction mixture is evaporated. The residue is taken up in MTBE and water. The aqueous phase is extracted three times with MTBE. The combined organic phases are dried over sodium sulfate, filtered and concentrated. After drying in vacuo 47 g (97% of theory) of product are obtained.

Aufarbeitung

  1. temperatureAfter 3 h under reflux
  2. customThe reaction mixture is evaporated
  3. extractionThe aqueous phase is extracted three times with MTBE
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter drying in vacuo 47 g (97% of theory) of product
  8. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-bf03baa7d5374c4e832a638e0886642c
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446102B2

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