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Methanol → 3-[1-(4-Acetylamino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester

HRID 2240600
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2240600
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH:11]=1.O(OC(C)=O)[O:23][C:24]([CH3:26])=O.C(N(CC)CC)C.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:24](=[O:23])[CH3:26])=[CH:17][CH:18]=2)[CH2:9][CH2:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 19362196Acetate oxygenHCID 574434273-[1-(4-Amino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-propionic acid methyl ester

Produkt 1

HCID 574434283-[1-(4-Acetylamino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl esterAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

17.5 mg of 3-[1-(4-amino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-propionic acid methyl ester (h) prepared by above Step 1 was dissolved in methylene chloride solution (0.06 mM). And then 6 μl of (AcO)2O (0.07 mM), 0.01 ml of triethylamine (0.08 mM) and 1.0 mg of DMAP (0.008 mM) were added thereto and the mixture was stirred for 3 hrs at 0° C. The reaction was stopped by adding methanol and the mixture was extracted three times with 10 ml of ethyl acetate. The organic layer was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with ethylacetate as an eluant to give 46 mg of 3-[1-(4-acetylamino-benzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester (i) (yield: 44%).

Aufarbeitung

  1. extractionthe mixture was extracted three times with 10 ml of ethyl acetate
  2. washThe organic layer was washed with saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting compound was purified with Silica gel column chromatography with ethylacetate as an eluant

Quellen und Nachweise

ORD-Eintrag
ord-cff8dbc8988a4c019549db026386126f
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07723376B2

Notizen zur Reaktion

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