Potassium Carbonate → 2-(Dipropylamino)-2-oxoethyl 3-(((benzyloxy)carbonyl)amino)propanoate

HRID 2406145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2406145
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH3:16])C(O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].Cl[CH2:24][C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26]>CN(C=O)C.O>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[C:25]([CH2:24][O:18][C:17](=[O:20])[CH2:16][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:26])[CH2:29][CH3:30]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 95657N-(Benzyloxycarbonyl)-DL-alanineHCID 2196472-chloro-N,N-dipropylacetamide

Produkt 1

HCID 667979022-(Dipropylamino)-2-oxoethyl 3-(((benzyloxy)carbonyl)amino)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of benzyloxycarbonylamino-propionic acid (22.3 g, 99.9 mmol) in DMF (150 ml) was added potassium carbonate (19.3 g, 139.9 mmol). 2-Chloro-N,N-dipropyl-acetamide (17.7 g, 99.9 mmol) was added over 30 min, and the reaction mixture was heated to 60° C. and stirred for 2.5 h. The reaction mixture was allowed to cool to RT and diluted with water (500 ml) and extracted with isopropyl acetate (total 500 ml). The combined organic phases were washed with water (3×200 ml) to afford a solution of 3-benzyloxycarbonylamino-propionic acid dipropylcarbamoylmethyl ester in isopropyl acetate which was not isolated further. LC-MS; 365.2 [M+H]+ Method (i)

Aufarbeitung

  1. temperatureto cool to RT
  2. extractionextracted with isopropyl acetate (total 500 ml)
  3. washThe combined organic phases were washed with water (3×200 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b8bf382323914e69bb2b9bd4c237fa1b
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809340B2

Notizen zur Reaktion

Wird geladen…