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Imidazole → (3R)-6-cyclohexyl-N-hydroxy-3-[3-(4-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanamide

HRID 1279801
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1279801
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:16]=2)[CH2:11][C:12](O)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.C[Si](C)(C)[O:41][NH2:42].N1C=CN=C1>ClCCl.C(OCC)(=O)C.CO>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:16]=2)[CH2:11][C:12]([NH:42][OH:41])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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Komponenten

8

Edukt 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 16747827(3R)-6-cyclohexyl-3-[3-(4-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid

Produkt 1

HCID 16749000(3R)-6-cyclohexyl-N-hydroxy-3-[3-(4-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanamideAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (3R)-6-cyclohexyl-3-[3-(4-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid (Preparation 106) (380 mg, 0.96 mmol) in dichloromethane (10 ml) was treated with 1,1′-carbonyldiimidazole (156 mg, 0.96 mmol) and stirred under a nitrogen atmosphere for 1 hour. O-(Trimethylsilyl)hydroxylamine (388 μl, 2.89 mmol) was added and the mixture was stirred for 3.5 hours. The mixture was then treated with methanol (5 ml) and stirred at room temperature for 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 95:5 (dichloromethane:methanol) to afford a white solid. Analysis suggests that 10% imidazole remains. The solid was dissolved in ethyl acetate and washed with water, dried over anhydrous magnesium sulphate, filtered and the solvent was removed under reduced pressure to afford the title compound as a white solid (128 mg).

Aufarbeitung

  1. stirringthe mixture was stirred for 3.5 hours
  2. stirringstirred at room temperature for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel eluting with 95:5 (dichloromethane:methanol)
  10. customto afford a white solid
  11. washwashed with water
  12. dry with materialdried over anhydrous magnesium sulphate
  13. filtrationfiltered
  14. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8567d5fbe36547538740a08afe1e451f
Quelldatensatz
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06448278B2

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