Ethylmorpholine → 3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide

HRID 133086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133086
C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=O)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[NH2:36][CH:37]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=1)[C:38]([N:40]([CH2:44][CH:45]([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48])[CH:41]([CH3:43])[CH3:42])=[O:39]>CN(C=O)C.C(Cl)CCl>[Cl:59][C:56]1[CH:55]=[CH:54][C:53]([CH2:52][CH:37]([NH:36][C:33](=[O:35])[CH2:32][CH2:31][NH:30][S:27]([C:24]2[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=2)(=[O:28])=[O:29])[C:38]([N:40]([CH2:44][CH:45]([O:46][CH2:47][CH3:48])[O:49][CH2:50][CH3:51])[CH:41]([CH3:42])[CH3:43])=[O:39])=[CH:58][CH:57]=1

Komponenten

7

Edukt 4

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 7573773-(4-Methoxy-benzenesulfonylamino)-propionic acidHCID 673416462-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

Produkt 1

HCID 684528403-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

52 mg of EDC, 45 mg of HOBt and 100 μl of N-ethylmorpholine are added to a solution of 124 mg of 3-(4-methoxybenzenesulfonylamino)propionic acid in 1 ml of DMF. A solution of 100 mg of 2-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide in 1 ml of DMF is added dropwise thereto, and the mixture is left to stir for 12 h. The reaction solution is filtered, mixed with ethyl acetate and then extracted with 5% aqueous sodium bicarbonate solution and aqueous sodium chloride solution. Drying of the organic phase with Chromabond XTR is followed by concentration under reduced pressure, and the residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The desired product is obtained with MW=598.16 (calculated); measured value (M−C2H6O+H)+: 552.1

Aufarbeitung

  1. waitthe mixture is left
  2. filtrationThe reaction solution is filtered
  3. additionmixed with ethyl acetate
  4. extractionextracted with 5% aqueous sodium bicarbonate solution and aqueous sodium chloride solution
  5. customDrying of the organic phase with Chromabond XTR
  6. concentrationis followed by concentration under reduced pressure
  7. customthe residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

Quellen und Nachweise

ORD-Eintrag
ord-c7b9a3523c92451e9f69af6bb8d821d6
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390814B2

Notizen zur Reaktion

Wird geladen…