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Sodium Dithionite → HCID 66546822, Verbindung

HRID 1746929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1746929
[C:1]([C:4]1[O:8][C:7]2[C:9](=[O:18])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[C:19]([O:23][C:24]([NH:26][CH2:27][C:28](O)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[Zn].C(OCC)(=O)C>[C:1]([C:4]1[O:8][C:7]2[C:9]([O:18][C:28](=[O:29])[CH2:27][NH:26][C:24]([O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:25])=[C:10]3[C:15](=[C:16]([OH:17])[C:6]=2[CH:5]=1)[CH:14]=[CH:13][CH:12]=[CH:11]3)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 24489Sodium DithioniteHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 103318442-Acetylfuro-1,4-naphthoquinone

Produkt 1

HCID 66546822HCID 66546822, VerbindungAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 250 ml round-bottom flask, 2 grams (8.3 mmoles) of 2-acetyl-naphtho[2,3-b]furan-4,9-dione (prepared in example 2 or 3) was dissolved in 50 ml of DMF with heating. To the solution, added 3.5 ml of TEA, 2 grams of zinc powder, 0.3 gram of tetrabutylammonium bromide, 2.33 grams (13.3 mmoles) of [(tert-butoxycarbonyl)amino]acetic acid, 5.04 grams (13.3 mmoles) of N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) and 7.25 grams (41.7 mmoles) of sodium hydrosulfite. The mixture was sealed or isolated from air, and then had been stirred vigorously at room temperature overnight. After addition of 100 ml of ethyl acetate, the reaction mixture was filtered, and the solid was washed with 50 ml of ethyl acetate. The filtrates were combined, extracted with 100 ml of ice-cooled aqueous 3% citric acid solution twice, and dried with anhydrous sodium sulfate. The organic phase was evaporated to dryness. Product was purified by silica gel chromatograph using dichloromethane/ethyl acetate (4:1) as elution solvent. 1.64 gram (4.1 mmoles) of product was obtained with yield of 49.4% and characterized by 1H NMR and mass spectrum. 1H NMR (in DMSO) δ 1.44 (s, 9H), 2.59 (s, 3H), 4.28 (d, J=6, 2H), 7.49-7.65 (m, 3H), 7.97 (m, 1H), 8.20-8.35 (m, 2H), 11.4 (s, 1H). Mass (M+H) is 400, Mass [M-(tert-butyl)+2H] is 344.

Aufarbeitung

  1. temperaturewith heating
  2. customThe mixture was sealed
  3. customisolated from air
  4. filtrationthe reaction mixture was filtered
  5. washthe solid was washed with 50 ml of ethyl acetate
  6. extractionextracted with 100 ml of ice-
  7. temperaturecooled aqueous 3% citric acid solution twice
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe organic phase was evaporated to dryness
  10. customProduct was purified by silica gel chromatograph
  11. washas elution solvent

Quellen und Nachweise

ORD-Eintrag
ord-c6d433455e0941ab8b4048c632d1ac28
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150530B2

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