Trifluoroacetic acid → (2R)-2-Methyl-amino-3-phenyl-N-((2-tetrahydrofuranyl)methyl)propionamide

HRID 1601944

Reaktionsgleichung

Reaktionsgleichung von HRID 1601944
C(OC(=O)[N:7](C)[C@@H:8]([C:16](=[O:24])[NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.F[C:28](F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:28][C@@:8]([NH2:7])([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]([NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1)=[O:24]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 10791Sodium SesquicarbonateHCID 516892Sodium BicarbonateHCID 10737368Methyl-((1R)-2-phenyl-1-((tetrahydrofuran-2-ylmethyl)carbamoyl)ethyl)carbamic acid tert-butyl ester

Produkt 1

HCID 69742982(2R)-2-Methyl-amino-3-phenyl-N-((2-tetrahydrofuranyl)methyl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methyl-((1R)-2-phenyl-1-((tetrahydrofuran-2-ylmethyl)carbamoyl)ethyl)carbamic acid tert-butyl ester (5.5 g; 15.2 mmol) was dissolved in methylene chloride (20 mL) and trifluoroacetic acid (20 mL) was added. The reaction mixture was stirred for 1 hour at room temperature. Methylene chloride (100 mL) and an aqueous solution of sodium hydrogen carbonate/sodium carbonate (pH 9, 50 mL) were added and solid sodium hydrogen carbonate was added until pH 8. The aquous phase was extracted with methylene chloride (100 mL) and the combined organic phases were dried (magnesium sulfate). The solvent was removed in vacuo to afford 3.62 g of (2R)-2-Methyl-amino-3-phenyl-N-((2-tetrahydrofuranyl)methyl)propionamide.

Aufarbeitung

  1. extractionThe aquous phase was extracted with methylene chloride (100 mL)
  2. dry with materialthe combined organic phases were dried (magnesium sulfate)
  3. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6db529ab369e451cb302821a303cb93b
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977178

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