Ethyl Acetate → 2-[(2-bromo)acetyl]amino-3-(1H-indol-3-yl)1-[N-(2-methoxybenzyl)acetylamino]propane

HRID 2086757

Reaktionsgleichung

Reaktionsgleichung von HRID 2086757
[NH2:1][CH:2]([CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)[CH2:3][NH:4][C:5](=[O:16])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15].C(N(C(C)C)CC)(C)C.[Br:36][CH2:37][C:38](Br)=[O:39].C(OCC)(=O)C>O1CCCC1>[Br:36][CH2:37][C:38]([NH:1][CH:2]([CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)[CH2:3][NH:4][C:5](=[O:16])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[O:39]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 225089552-amino-3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]propane

Produkt 1

HCID 697369492-[(2-bromo)acetyl]amino-3-(1H-indol-3-yl)1-[N-(2-methoxybenzyl)acetylamino]propane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-amino-3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]propane (7.51 g, 21.369 mmoles) in anhydrous tetrahydrofuran (100 ml) under a nitrogen atmosphere at 0° C. was added diisopropylethylamine (4.1 ml, 23.537 mmoles) and bromoacetyl bromide (2.05 ml, 23.530 mmoles). After 2 hours, ethyl acetate was added and the reaction mixture washed with water twice, 1.0 N hydrochloric acid (2×), saturated sodium bicarbonate solution (2×), and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to a tan foam on a rotary evaporator. In this manner the 2-[(2-bromo)acetyl]amino-3-(1H-indol-3-yl)-1-[N-(2-methoxybenzyl)acetylamino]propane was obtained in quantitative yield. No further purification was necessary.

Aufarbeitung

  1. washthe reaction mixture washed with water twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a tan foam on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-b9dd199aacf54fafb5827981dd0c8e9a
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727255B1

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