Trifluoroacetic acid → (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}6-cyclohexylhexanoic acid

HRID 2183051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183051
[NH2:1][C:2](=[O:29])[CH2:3][O:4][CH2:5][C:6]1[N:10]=[C:9]([C@H:11]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[O:8][N:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2](=[O:29])[CH2:3][O:4][CH2:5][C:6]1[N:10]=[C:9]([C@H:11]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:12][C:13]([OH:15])=[O:14])[O:8][N:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59909799tert-Butyl (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate

Produkt 1

HCID 59909790(3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}6-cyclohexylhexanoic acidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate (Preparation 90) (280 mg, 0.86 mmol) in dichloromethane (7 ml) was treated with trifluoroacetic acid (3 ml) and stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene and dichloromethane. The oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:acetic acid) gradually changing to 90:10:1 (dichloromethane:methanol:acetic acid) to afford a colourless oil which was triturated with diethyl ether and filtered to afford the title compound (155 mg).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene and dichloromethane
  3. customThe oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:acetic acid)
  4. customto afford a colourless oil which
  5. customwas triturated with diethyl ether
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-423d3b810eb440a9ae14b1c2a2e97ab4
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897306B2

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