Trifluoroacetic acid → (2R)-3-(1,1'-biphenyl-4-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide

HRID 366202

Reaktionsgleichung

Reaktionsgleichung von HRID 366202
C(O[C:6](=O)[N:7]([C@@H:9]([C:23](=[O:38])[N:24]([CH3:37])[C@@H:25]([C:33](=[O:36])[NH:34][CH3:35])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)C)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:13]=[CH:12][C:11]([CH2:10][C@@H:9]([NH:7][CH3:6])[C:23]([N:24]([CH3:37])[C@@H:25]([C:33](=[O:36])[NH:34][CH3:35])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:38])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 10791Sodium SesquicarbonateHCID 516892Sodium BicarbonateHCID 10530245((1R)-2-(1,1'-Biphenyl-4-yl)-1-(methyl-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)ethyl)methyl-carbamic acid tert-butylester

Produkt 1

HCID 10812511(2R)-3-(1,1'-biphenyl-4-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamideAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

((1R)-2-(1,1'-Biphenyl-4-yl)-1-(methyl-((1R)-1-(methylcarbamoyl)-2-phenylethyl)-carbamoyl)ethyl)methyl-carbamic acid tert-butylester (1.0 g; 1.8 mmol) was dissolved in methylene chloride (4 mL). Trifluoroacetic acid (4 mL) was added and the reaction mixture was stirred for 15 min at room temperature. Methylene chloride (40 mL), an aqueous solution of sodium hydrogen carbonate/sodium carbonate (pH 9; 40 mL) and sodium hydrogen carbonate (solid) were added to the reaction mixture until pH 9. The organic phase was dried (magnesium sulfate) and the solvent was removed in vacuo to afford 0.76 g of (2R)-3-(1,1'-biphenyl-4-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide.

Aufarbeitung

  1. dry with materialThe organic phase was dried (magnesium sulfate)
  2. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1af3dd60570a4617b11cb3134442c4cb
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127391

Verknüpfte Notizen

Wird geladen…