Dicyclohexylcarbodiimide → HCID 68526655, Verbindung

HRID 2247641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247641
[Si]([O:8][CH2:9][C:10]1[O:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[CH:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=O)=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.CCOCC.O1CCCC1.O>[CH:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29]3[O:18][N:17]=[C:15]([C:13]4[O:14][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=4)[N:16]=3)=[CH:27][CH:26]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Komponenten

9

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 883374-Cyclohexylbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 866202115-({[t-Butyl(dimethyl)silyl]oxy}methyl)-N'-hydroxyfuran-2-carboximidamide

Produkt 1

HCID 68526655HCID 68526655, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxyfuran-2-carboximidamide (0.19 g, 0.70 mmol) that was obtained in Example 2 (2b), 4-cyclohexylbenzoic acid (0.16 g, 0.77 mmol), and N,N′-dicyclohexylcarbodiimide (0.17 g, 0.84 mmol) in dichloromethane (1.5 ml) was stirred for 1 hour. After stirring, the reaction mixture was diluted with ether, and insoluble materials were removed by filtration with Celite, and then the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue obtained in tetrahydrofuran (1.0 ml) was added tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 1.1 ml, 1.1 mmol) with stirring, and the resulting mixture was stirred at 60° C. for 1 hour. After stirring, the reaction mixture was poured into water (20 ml) to quench the reaction and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (0.18 g) in a yield of 81% as a white crystalline solid.

Aufarbeitung

  1. stirringAfter stirring
  2. customwere removed by filtration with Celite
  3. customthe filtrate was evaporated in vacuo
  4. customSubsequently, to a solution of the residue obtained in tetrahydrofuran (1.0 ml)
  5. stirringwith stirring
  6. stirringthe resulting mixture was stirred at 60° C. for 1 hour
  7. stirringAfter stirring
  8. customto quench
  9. customthe reaction
  10. extractionextracted with ether
  11. washThe extract was washed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. filtrationAfter filtration
  14. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d51d45d376004d03ae01720d3f99ff56
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687491B2

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