Triphenylphosphine → Ethyl 3-phenyl-3-(6-{3-[(pyridin-2-yl)(2,2,2-trichloroethoxycarbonyl) amino]propoxy}indol-3-yl)propionate

HRID 351927

Reaktionsgleichung

Reaktionsgleichung von HRID 351927
[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][CH2:25][CH2:26]O)=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:28][C:29]([Cl:42])([Cl:41])[CH2:30][O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)=[O:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][CH2:25][CH2:26][N:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[C:32]([O:31][CH2:30][C:29]([Cl:28])([Cl:41])[Cl:42])=[O:33])=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 116876422,2,2-Trichloroethyl pyridin-2-ylcarbamateHCID 15549282Ethyl 3-phenyl-3-[6-(3-hydroxypropoxy)indol-3-yl]propionate

Produkt 1

HCID 15549283Ethyl 3-phenyl-3-(6-{3-[(pyridin-2-yl)(2,2,2-trichloroethoxycarbonyl) amino]propoxy}indol-3-yl)propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

500 mg (1.36 mmol) of 5 and 550 mg (2.04 mmol) of 2-(2,2,2-trichloroethoxycarbonylamino)pyridine and 907 mg (2.72 mmol) of triphenylphosphine (polymer-bound) are introduced into 7.5 ml of anhydrous THF, and a solution of 0.32 ml (2.04 mmol) of azodicarboxylic acid diethyl ester (diethyl azodicarboxylate, DEAD) in 7.5 ml of THF is added dropwise at room temperature over the course of 30 minutes. The TLC check shows complete conversion after 1.5 hours. The polymer is filtered off, and the solution is washed with a little water, dried and evaporated. The residue can be purified by chromatography on silica gel (eluent gradient toluene/acetone 20:1→4:1), giving ethyl 3-phenyl-3-(6-{3-[(pyridin-2-yl)(2,2,2-trichloroethoxycarbonyl)amino]propoxy}indol-3-yl)propionate.

Aufarbeitung

  1. customafter 1.5 hours
  2. filtrationThe polymer is filtered off
  3. washthe solution is washed with a little water
  4. customdried
  5. customevaporated
  6. customThe residue can be purified by chromatography on silica gel (eluent gradient toluene/acetone 20:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6368bd859e1d47f7bc07fce48a640c73
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743810B2

Verknüpfte Notizen

Wird geladen…