Trifluoroacetic acid → Ethyl 4-{3-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]propyl}benzoate

HRID 2181492

Reaktionsgleichung

Reaktionsgleichung von HRID 2181492
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH2:24][CH2:25][NH:26][S:27]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)(=[O:29])=[O:28])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.[CH2:46]([O:48][C:49](=[O:60])[C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57][CH:58]=O)=[CH:52][CH:51]=1)[CH3:47].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:58][CH2:57][CH2:56][C:53]2[CH:54]=[CH:55][C:50]([C:49]([O:48][CH2:46][CH3:47])=[O:60])=[CH:51][CH:52]=2)=[C:15]1[CH2:24][CH2:25][NH:26][S:27]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)(=[O:28])=[O:29])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 2757377Ethyl 4-(3-oxopropyl)benzoateHCID 11204051N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)methanesulfonamide

Produkt 1

HCID 11239705Ethyl 4-{3-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]propyl}benzoateAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution N-[2-(1-benzhydryl-5-chloro-1H-indol-2-yl)ethyl]-1-(3,4-dichlorophenyl)-methanesulfonamide (3.0 g, 5.14 mmol), triethylsilane (1.79 g, 15.4 mmol), and 4-(3-oxopropyl)benzoic acid ethyl ester (1.26 g, 6.16 mmol) in dichloromethane (30 mL) at −20 to −25° C. was added trifloroacetic acid (2.93 g, 25.7 mmol) during a period of 1 min. The mixture was warmed to −10° C. and stirred for 4 h. Saturated aqueous NaHCO3 (20 mL) was added. The mixture was extracted with EtOAc (150 mL). The organic extract was dried over Na2SO4. The solvent is evaporated. The residue is purified by column chromatography, using a mixture of heptane and EtOAc (4:1) as elute to give a white solid (2.25 g, 56%). 1H NMR (CDCl3): δ6.9-7.6 (m, Ph, CHPh2), 7.97 (d, 1H, J=1.6 Hz), 7.41 (d, 1H, J=1.9 Hz), 6.50 (d, 1H, J=8.9 Hz), 4.35 (dd, 2H, J=7.1, 14.3 Hz), 4.13 (m, 1H), 3.92 (s, 2H), 2.95 (m, 2H), 2.71 (m, 6H), 1.96 (m, 2H), 1.38 (t, 3H, J=7.1 Hz).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (150 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customThe solvent is evaporated
  5. customThe residue is purified by column chromatography
  6. additiona mixture of heptane and EtOAc (4:1)
  7. washas elute

Quellen und Nachweise

ORD-Eintrag
ord-0e5fa3af0a094916b94b536be6a48861
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06891065B2

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