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Water → (R)-3-(6-Chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2175192
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C@@H:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13].CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C@@H:17]([NH:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 915086(R)-Ethyl 3-amino-3-phenylpropanoate

Produkt 1

HCID 58497459(R)-3-(6-Chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl esterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2,6-dichloro-3-nitro-pyridine (0.75 g, 3.58 mmol) in DMF (30 ml) were added (R)-3-amino-3-phenylpropanoic acid ethyl ester (0.83 g, 4.29 mmol) and DIPEA (1.25 ml, 7.15 mmol). The reaction mixture was stirred at 70° C. overnight after which time it was poured into water (200 ml) and EtOAc. The layers were separated and the aqueous phase was extracted once more with EtOAc. The combined organics were washed with water twice and dried (MgSO4). Filtered and concentrated to give the crude product as an orange oil which was then purified by silica gel flash column chromatography (12 g silica gel, 5% EtOAc/Hexane) to afford 0.80 g (64%) of the title compound as a orange oil which was used without further purification.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted once more with EtOAc
  3. washThe combined organics were washed with water twice
  4. dry with materialdried (MgSO4)
  5. filtrationFiltered
  6. concentrationconcentrated
  7. customto give the crude product as an orange oil which
  8. customwas then purified by silica gel flash column chromatography (12 g silica gel, 5% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d06c900b10ad4bcf883d0c15f0078b8d
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09062056B2

Notizen zur Reaktion

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