StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Nitromethane → 1-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-3-nitropropan-2-one

HRID 2042930
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2042930
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][C:48](O)=[O:49].C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:63]([CH3:66])([O-:65])=[O:64].[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47][C:48](=[O:49])[CH2:66][N+:63]([O-:65])=[O:64]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6375NitromethaneHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 67289388HCID 67289388, Verbindung

Produkt 1

HCID 866808891-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-3-nitropropan-2-oneAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a anhydrous THF (22 mL) solution of the carboxylic acid 55 (2.97 g, 4.28 mmol) was added 1,1′-carbonyl diimidazole (800 mg, 4.93 mmol) at room temperature. In separate flask, nitromethane (0.92 mL, 17.12 mmol) was added to a THF (9 mL) solution of NaH (200 mg, 4.93 mmol). The resulting white suspension was stirred at room temperature for 3 h. Then the prepared acyl imidazole solution was added to the suspension through a cannula at room temperature. After the transfer, the mixture was heated to 50° C. for 1.5 h. It was cooled to room temperature and quenched with 1.0 M HCl. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound (3.13 g, 99%).

Aufarbeitung

  1. temperatureAfter the transfer, the mixture was heated to 50° C. for 1.5 h
  2. temperatureIt was cooled to room temperature
  3. customquenched with 1.0 M HCl
  4. extractionThe organic layer was extracted with ethyl acetate
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-23aed3c3f7b94636b8fbd67895b4048f
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586550B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion