1H-Indole-3-propanoic acid → HCID 18923870, Verbindung

HRID 1290261

Reaktionsgleichung

Reaktionsgleichung von HRID 1290261
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12](O)=O)=[CH:2]1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[O:36]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[O:39][CH2:38][CH:37]1[CH2:46][NH2:47]>CN(C=O)C>[O:36]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[O:39][CH2:38][CH:37]1[CH2:46][NH:47][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Komponenten

6

Edukt 4

HCID 37441H-Indole-3-propanoic acidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochloride

Produkt 1

HCID 18923870HCID 18923870, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3-Indolepropionic acid (1.1 g, 6.0 mmole), 1-hydroxybenzotriazole hydrate (0.97 g, 7.2 mmole) and 1,3-diisopropylcarbodiimide (2.3 ml, 14.4 mmole) were combined in 100 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (1.2 g, 6.0 mmole) in 50 ml of DMF, and the mixture was further stirred for 24 hours. The solvent was removed and the residue partitioned between dichloromethane and water. The separated dichloromethane layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was chromatographed on a silica gel column using ethyl acetate as the eluant. Fractions containing product were concentrated and washed with a minimum amount of THF to remove a by-product and to give 1.2 g (60%) of the desired product, (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-4-(1H-indol-3-yl)-propanamide, as an oily solid.

Aufarbeitung

  1. stirringthe mixture was further stirred for 24 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between dichloromethane and water
  4. dry with materialThe separated dichloromethane layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was chromatographed on a silica gel column
  8. additionFractions containing product
  9. concentrationwere concentrated
  10. washwashed with a minimum amount of THF
  11. customto remove a by-product

Quellen und Nachweise

ORD-Eintrag
ord-b52a2b3c0a8e4215b363f35511ac5223
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750724

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