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

Sodium hydride → [2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl ester

HRID 2075650
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2075650
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH:45]=[C:46]([O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH:47]=1)[O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][OH:44])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:71]([O:75][C:76](=[O:79])[CH2:77]Br)([CH3:74])([CH3:73])[CH3:72]>C1COCC1.CN(C=O)C.C1COCC1>[C:71]([O:75][C:76](=[O:79])[CH2:77][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][C:28]1[CH:27]=[C:26]([O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:47]=[C:46]([O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH:45]=1)([CH3:74])([CH3:73])[CH3:72]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 586877452-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol

Produkt 1

HCID 86607046[2-(2-{2-[2-(2-{3,5-Bis-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-acetic acid tert-butyl ester
Ausbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To an ice-cooled suspension of sodium hydride (175 mg, 4.4 mmol; 60% in mineral oil) in THF/DMF (4/1 mixed fluid 5 ml), a solution of Compound 47 (1.05 g, 1.09 mmol) in THF (5 ml) was gradually added, and this was followed by stirring for 30 minutes. A solution of bromoacetic acid tert-butyl ester (847 mg, 4.3 mmol) in THF (6 ml) was added thereto. After the ice bath was removed, stirring was further conducted at room temperature for 2 hours. Water was carefully added to stop the reaction, and this was followed by extraction from ethyl acetate, and the combined organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. Filtration and concentration under reduced pressure were conducted, after which the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate solution containing 5% methanol)) to yield Compound 48 (light-yellow oil 530 mg, 45%).

Aufarbeitung

  1. customAfter the ice bath was removed
  2. stirringstirring
  3. waitwas further conducted at room temperature for 2 hours
  4. additionWater was carefully added
  5. customthe reaction
  6. extractionthis was followed by extraction from ethyl acetate
  7. washthe combined organic phases were washed with saturated brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationFiltration and concentration under reduced pressure
  10. customafter which the residue obtained
  11. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (ethyl acetate-ethyl acetate solution containing 5% methanol))

Quellen und Nachweise

ORD-Eintrag
ord-f4c1185b2c8144989018ab4be32b6635
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919653B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion