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Triethylamine → tert-Butyl (3R)-6-cyclohexyl-3-(3-{[3-(4-morpholinyl)-1-azetidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoate

HRID 2182989
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2182989
[C:1]([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([C:23](OCC)=[O:24])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH:31]1[CH2:34][CH:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH2:32]1.C(N(CC)CC)C>C(O)C>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([C:23]([N:31]3[CH2:34][CH:33]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[CH2:32]3)=[O:24])[N:19]=2)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 220613264-(Azetidin-3-yl)morpholine dihydrochlorideHCID 59909797ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate

Produkt 1

HCID 59909782tert-Butyl (3R)-6-cyclohexyl-3-(3-{[3-(4-morpholinyl)-1-azetidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoateAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

A solution of ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (1.00 g, 2.54 mmol) in ethanol (10 ml) was treated with 4-(3-azetidinyl)morpholine dihydrochloride (2.72 g, 12.6 mmol) and triethylamine (2.56 g, 25 mmol) and the resulting mixture was heated under reflux under a nitrogen atmosphere for 24 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed sequentially with water and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (97:3) gradually changing to dichloromethane:methanol (95:5) to afford the title compound as a colourless oil (1.32 g).

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 24 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed sequentially with water and brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (97:3)

Quellen und Nachweise

ORD-Eintrag
ord-ba94b245e3854b339a85315d6393c1b8
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06897306B2

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