Ethyl 3-(methylamino)propanoate → 3-{Methyl[(3-methyl-4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoic acid

HRID 1877131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877131
C[C:2]1[CH:10]=[C:9]([NH:11][CH:12]([C:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:18]=2[CH3:28])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:29][NH:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34].Cl.[CH2:39](N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:29][N:30]([C:4]([C:3]1[CH:7]=[CH:8][C:9]([NH:11][CH:12]([C:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:18]=2[CH3:28])[CH2:13][CH:14]([CH3:16])[CH3:15])=[C:10]([CH3:39])[CH:2]=1)=[O:5])[CH2:31][CH2:32][C:33]([OH:35])=[O:34]

Komponenten

8

Edukt 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68509237HCID 68509237, VerbindungHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 595294323-{Methyl[(3-methyl-4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}benzoic acid (228 mg), ethyl 3-(methylamino)propanoate (94 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg), hydroxybenzotriazole monohydrate (110 mg) and triethylamine (100 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 (1.2 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 (271 mg, 97%).

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 (1.2 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-e3d7ce69aa0545c38b898bdb6576be7d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309580B2

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