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Ethyl 3-(methylamino)propanoate → HCID 59529576, Verbindung

HRID 1877182
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1877182
[CH:1]1([CH:7]([NH:25][C:26]2[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[N:15][C:16]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:17][CH:18]=3)[O:10][C:9]=2[CH3:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:35][NH:36][CH2:37][CH2:38][C:39]([O:41]CC)=[O:40].Cl.C(N=C=NCCCN(C)C)C.O.[OH:57][C:58]1C2N=NNC=2C=CC=1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([CH:7]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([C:58]([N:36]([CH3:35])[CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[O:57])=[CH:33][CH:34]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[N:15][C:16]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:17][CH:18]=3)[O:10][C:9]=2[CH3:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68511428HCID 68511428, VerbindungHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 59529576HCID 59529576, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-[(cyclohexyl{5-[6-(2-methoxyethoxy)pyridin-3-yl]-2-methylfuran-3-yl}methyl)amino]benzoic acid (232 mg), ethyl 3-(methylamino)propanoate (79 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg), hydroxybenzotriazole monohydrate (92 mg) and triethylamine (84 μL) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 4 hr. Ethyl acetate was added, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure. To the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.0 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (233 mg, 85%).

Aufarbeitung

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.0 mL)
  7. customThe solvent was evaporated under reduced pressure, and water (10 mL)
  8. additionwas added
  9. temperaturecooling
  10. stirringstirred for 1 hr
  11. filtrationThe resulting precipitate was collected by filtration
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-caa16e0c46af47b58dde3bad8cc75cdd
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309580B2

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