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Water → Ethyl 3-{[(4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

HRID 2091215
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2091215
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:27]=[CH:26][C:22](C(O)=O)=[CH:21][CH:20]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH3:28])[C:7]=2[CH:29]=1.CNC[CH2:33][C:34]([O:36]CC)=O.[OH2:39].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:56][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])C.[OH2:62]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:61]([N:59]([CH3:60])[CH2:58][CH2:57][C:56]([O:36][CH2:34][CH3:33])=[O:62])=[O:39])=[CH:26][CH:27]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:8]([CH3:28])[C:7]=2[CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 962WaterHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667776604-{[(5-Methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid

Produkt 1

HCID 66777122
Ethyl 3-{[(4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate
Ausbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of 4-{[(5-methoxy-3-methyl-1-benzofuran-2-yl)(phenyl)methyl]amino}benzoic acid (400 mg) synthesized above, ethyl 3-(methylamino)propanoate (203 mg), 1-hydroxybenzotriazole monohydrate (237 mg), triethylamine (431 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (297 mg), and the mixture was stirred overnight at room temperature. Water was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (486 mg, 94%) as a pale-brown oil

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-003c0fc8e5d243f0beb3730a24ecffbf
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436043B2

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