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

HRID 2261396
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2261396
[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.C(Cl)Cl.O(OC(C)=O)[O:26][C:27]([CH3:29])=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CO>[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:27](=[O:26])[CH3:29])=[CH:17][CH:18]=2)[CH2:9][CH2:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 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 229,4 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 887MethanolLösungsmittel

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 mmol). And then 6 μl of (AcO)2O (0.07 mmol), 0.01 ml of triethylamine (0.08 mmol) and 1.0 mg of DMAP (0.008 mmol) 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-805b35436e954f028fe9de1a3e60b145
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07846963B2

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