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9-Fluorenylmethyl chloroformate → HCID 22872534, Verbindung

HRID 1779970
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1779970
COC1[C@@H](C(C)C)N=[C:6]([O:12][CH3:13])[C@H:7]([CH2:9][O:10][CH3:11])[N:8]=1.[C:17](Cl)([O:19][CH2:20][CH:21]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18].C([O-])(O)=[O:36].[Na+]>O1CCOCC1.O.C(Cl)(Cl)Cl>[CH:32]1[C:33]2[CH:21]([CH2:20][O:19][C:17]([NH:8][C@@H:7]([CH2:9][O:10][CH3:11])[C:6]([O:12][CH3:13])=[O:36])=[O:18])[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]=2[CH:29]=[CH:30][CH:31]=1
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Komponenten

7

Edukt 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 57294432HCID 57294432, Verbindung

Produkt 1

HCID 22872534HCID 22872534, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212
Chloroform
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2R,5S)-3,6-dimethoxy-5-(methoxymethyl)-2-isopropyl-2,5-dihydropyrazine (2.1 g, 9.2 mmol) in dioxane (18 ml ) 1M HCl (18.4 ml ), 18.4 mmol) was added and the mixture stirred at ambient temperature overnight. The volatile components were evaporated, the residue redissolved in dioxane and again evaporated. The crude residue was dissolved dioxane and FmocCl (5.71 g, 2.21 mmol) was added. After 2 minutes 1M NaHCO3 (44.2 ml, 44.2 mmol) was added. After 15 minutes the mixture was diluted with water (50 ml) and CHCl3 (100 ml). The layers were separated and the aqueous phase extracted with CHCl3 (2×75 ml). The combined organic layer was dried (Na2SO4), concentrated and purified by flash chromatography (silica gel; hexane: ethyl acetate 2:1).

Aufarbeitung

  1. customThe volatile components were evaporated
  2. dissolutionthe residue redissolved in dioxane
  3. customagain evaporated
  4. additionwas added
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with CHCl3 (2×75 ml)
  7. dry with materialThe combined organic layer was dried (Na2SO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography (silica gel; hexane: ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5073e6f75b62487185cd8679160e8b71
Quelldatensatz
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05629293

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