Trifluoroacetic acid → 2-Methyl-2-[3-(piperidin-4-ylcarbamoyl)-phenoxy]-propionic acid ethyl ester

HRID 502386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502386
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:31])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:25])[CH3:24])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:29]([O:28][C:26](=[O:27])[C:23]([CH3:25])([O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15](=[O:31])[NH:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:17]=1)[CH3:24])[CH3:30]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 684578994-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 684563992-Methyl-2-[3-(piperidin-4-ylcarbamoyl)-phenoxy]-propionic acid ethyl esterAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.08 g (5.0 mmol) of 4-[3-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester was dissolved under argon in 80 mL of MeCl2; to the stirred solution, 3.66 mL (5.46 g=10 eq.) of TFA was added drop by drop and stirring continued at rt for 5 h. Then, the reaction mixture was evaporated i.V., the residue was dissolved in MeCl2 and water, the pH was adjusted to ˜10 with sodium carbonate solution and the mixture was extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. The crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH) to yield 1.20 g of the title compound as colorless oil. MS: 335.2 (MH+).

Aufarbeitung

  1. customThen, the reaction mixture was evaporated i.V
  2. dissolution, the residue was dissolved in MeCl2
  3. extractionthe mixture was extracted twice with MeCl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated i.V
  8. customThe crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-06705bbc4a6b442d887aa0b1afd8a02f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

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