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Water → HCID 131728697, Verbindung

HRID 1892831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1892831
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:26]1C=CN=C1)=O.O.N.O>O1CCCC1.C(OCC)(=O)C>[NH2:26][C:11](=[O:12])[C@@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 12896473Azane;hydrateHCID 66935162(2S)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid

Produkt 1

HCID 131728697HCID 131728697, VerbindungAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(Step 3) To (2S)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid (30 g) in tetrahydrofuran (150 ml) solution, 1,1′-carbonyldiimidazole (15.6 g) was added under ice cooling and the mixture was stirred at room temperature for 1 hour. The reaction solution was cooled to 0° C., 28% ammonia water (30 ml) was added, and the mixture was stirred at room temperature for 30 minutes. Distilled water and ethyl acetate were added to the reaction solution, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was successively washed with saturated potassium hydrogensulfate aqueous solution and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. Hexane and ethyl acetate were added to the precipitated solid and the mixture was stirred in the suspended state at room temperature. The precipitated solid was collected by filtration to obtain the title compound (29.2 g).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customthe aqueous layer and the organic layer were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was successively washed with saturated potassium hydrogensulfate aqueous solution and saturated saline
  6. dry with materialdried over with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionHexane and ethyl acetate were added to the precipitated solid
  9. stirringthe mixture was stirred in the suspended state at room temperature
  10. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-5f3c6c4b852f45e3afb9e80b854b1c67
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507714B2

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