Trifluoroacetic acid → N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-beta-alanine

HRID 1631192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631192
[OH:1][CH2:2][CH:3]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1)[CH2:4][NH:5][CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9].NCCCC1C=CC(O)=CC=1.FC(F)(F)C(O)=O>ClCCl>[OH:1][CH2:2][CH:3]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:20][CH:21]=1)[CH2:4][NH:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 4574248HCID 4574248, VerbindungHCID 23121314tert-butyl N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-beta-alaninate

Produkt 1

HCID 23121697N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-beta-alanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-β-alaninate (65 mg; prepared by following the procedure of Example 4 using the compound prepared in Example 15 as a substitute for 4-(3-aminopropyl)phenol) in dichloromethane (3 mL), trifluoroacetic acid (3 mL) was dropped at 0° C., followed by stirring at room temperature for 2 hours. Then, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4). The crude product thus obtained was washed with diethyl ether to give the title compound (38 mg) having the following physical properties.

Aufarbeitung

  1. customprepared
  2. concentrationThen, the reaction mixture was concentrated
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4)
  4. customThe crude product thus obtained
  5. washwas washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-369e197636fb4f2bb89dba1aa9693362
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791159B2

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