Trifluoroacetic acid → (2R)-N-methyl-2-(methylamino)3-(2-naphthyl)-N-(2-(2-thienyl)ethyl)propionamide

HRID 650808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650808
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:20](=[O:30])[N:21]([CH3:29])[CH2:22][CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:29][N:21]([CH2:22][CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[C:20](=[O:30])[C@H:8]([NH:7][CH3:6])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 54259442N-methyl-N-((1R)-1-(N-methyl-N-(2-(2-thienyl)ethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamic acid tert-butyl ester

Produkt 1

HCID 10831847(2R)-N-methyl-2-(methylamino)3-(2-naphthyl)-N-(2-(2-thienyl)ethyl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Methyl-N-((1R)-1-(N-methyl-N-(2-(2-thienyl)ethyl)carbamoyl)-2-(2-naphthyl)ethyl)carbamic acid tert-butyl ester (5.17 g, 11.4 mmol was dissolved in dichloromethane (12 ml). The solution was cooled to 0° C. Trifluoroacetic acid (12 ml) was added. The reaction mixture was stirred for 15 min at 0° C. The solvent was removed in vacuo at 20° C. The residue was codistilled with dichloromethane (3×60 ml). The crude product was purified by flash chromatography on silica (80 g), using dichloromethane/methanol/125% aqueous (100:10:1) ammonia as eluent, to give 1.91 g of (2R)-N-methyl-2-(methylamino)3-(2-naphthyl)-N-(2-(2-thienyl)ethyl)propionamide.

Aufarbeitung

  1. customThe solvent was removed in vacuo at 20° C
  2. customThe crude product was purified by flash chromatography on silica (80 g)

Quellen und Nachweise

ORD-Eintrag
ord-cc053430f37d4294b802c06fa15574a9
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274584B1

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