Acetic Anhydride → 3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]-2-(N-triphenylmethylamino)propane

HRID 380676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380676
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([NH:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2OC)=[CH:2]1.C(N(CC)CC)C.[C:50]([O:53][C:54](=O)[CH3:55])(=O)C.[O:57]1CCCC1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([NH:23][C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:12][NH:13][C:14](=[O:57])[CH2:15][CH2:20][C:19]2[CH:18]=[CH:17][CH:16]=[CH:55][C:54]=2[O:53][CH3:50])=[CH:2]1

Komponenten

5

Edukt 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 107214113-(1H-indol-3-yl)1-[N-(2-methoxybenzyl)amino]-2-(N-triphenylmethylamino)propane

Produkt 1

HCID 225089513-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]-2-(N-triphenylmethylamino)propaneAusbeute 87 %

Versuchsvorschrift

To a stirring solution of 3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)amino]-2-(N-triphenylmethylamino)propane (0.404 mole) in anhydrous tetrahydrofuran (1.2 liters) under a nitrogen atmosphere at 0° C. was added triethylamine (66.5 ml, 0.477 mole) and acetic anhydride (45.0 ml, 0.477 mole). After 4 hours, the mixture was concentrated on a rotary evaporator, redissolved in methylene chloride and ethyl acetate, washed with water (2×) and brine (2×), dried over anhydrous sodium sulfate, filtered, and concentrated to a solid on a rotary evaporator. The resulting solid was dissolved in chloroform and loaded onto silica gel 60 (230-400 mesh) and eluted with a 1:1 mixture of ethyl acetate and hexanes. The product was then crystallized from an ethyl acetate/hexanes mixture. The resulting product of 3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]-2-(N-triphenylmethylamino)propane was crystallized and isolated over three crops giving 208.97 grams (87% yield) of analytically pure material.

Aufarbeitung

  1. concentrationthe mixture was concentrated on a rotary evaporator
  2. dissolutionredissolved in methylene chloride
  3. washethyl acetate, washed with water (2×) and brine (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a solid on a rotary evaporator
  7. dissolutionThe resulting solid was dissolved in chloroform
  8. washeluted with a 1:1 mixture of ethyl acetate and hexanes
  9. customThe product was then crystallized from an ethyl acetate/hexanes mixture
  10. customThe resulting product of 3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]-2-(N-triphenylmethylamino)propane was crystallized
  11. customisolated over three crops
  12. customgiving 208.97 grams (87% yield) of analytically pure material

Quellen und Nachweise

ORD-Eintrag
ord-7dfbe59c1aa14fbea6981e9cb54b362f
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303610B1

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