Diisopropylcarbodiimide → HCID 18923896, Verbindung

HRID 1290259

Reaktionsgleichung

Reaktionsgleichung von HRID 1290259
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][C:15](O)=O.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.Cl.[CH3:39][S:40]([NH:43][C:44]1[CH:45]=[CH:46][C:47]2[O:52][CH2:51][CH:50]([CH2:53][NH2:54])[O:49][C:48]=2[CH:55]=1)(=[O:42])=[O:41]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][NH:54][CH2:53][CH:50]1[CH2:51][O:52][C:47]2[CH:46]=[CH:45][C:44]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])=[CH:55][C:48]=2[O:49]1

Komponenten

6

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112417775-Methoxyindole-3-butyric acidHCID 18923878HCID 18923878, Verbindung

Produkt 1

HCID 18923896HCID 18923896, VerbindungAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

5-Methoxyindole-3-butyric acid (0.75 g, 3.2 mmole), 1-hydroxybenzotriazole hydrate (0.52 g, 3.8 mmole) and 1,3-diisopropylcarbodiimide (1.2 ml, 7.6 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 7-methylsulfonylamino-2,3-dihydro-1,4-benzodioxin-2-methanamine hydrochloride (0.9 g, 3.2 mmole) in 50 ml of DMF and the mixture was further stirred for 48 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 first ethyl acetate and then 2.5% methanol in ethyl acetate as eluants. Fractions were concentrated and washed with a minimum amount of THF to remove a byproduct and to give 1.2 g (79%) of the desired product, (7-methylsulfonyl amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-4-(5-methoxy-1H-indol-3-yl)-butanamide, as a oily white solid.

Aufarbeitung

  1. stirringthe mixture was further stirred for 48 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. concentrationFractions were concentrated
  9. washwashed with a minimum amount of THF
  10. customto remove a byproduct

Quellen und Nachweise

ORD-Eintrag
ord-98e0c3e57b804102b93f3736b2399dc3
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750724

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