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Thionyl Chloride → HCID 18633406, Verbindung

HRID 1085536
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1085536
[CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[N:7]([CH:17]=1)[C@@H:8]1[O:16][C@H:12]([CH2:13][NH:14][CH3:15])[C@@H:10]([OH:11])[CH2:9]1)[CH3:2].[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28](Cl)=[O:29].S(Cl)(Cl)=O>N1C=CC=CC=1.C1C=CC=CC=1.C(Cl)Cl.CO>[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28]([N:14]([CH2:13][C@H:12]1[O:16][C@@H:8]([N:7]2[CH:17]=[C:3]([CH2:1][CH3:2])[C:4](=[O:19])[NH:5][C:6]2=[O:18])[CH2:9][C@@H:10]1[OH:11])[CH3:15])=[O:29]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 24386Thionyl ChlorideHCID 41383862-Bromophenylacetyl chlorideHCID 18633445HCID 18633445, Verbindung

Produkt 1

HCID 18633406HCID 18633406, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittel2×
HCID 1049
Pyridine
Lösungsmittel
HCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.72 g of 2',5'-dideoxy-5-ethyl-5'-methylaminouridine in 25 ml of dry pyridine was stirred at 0° C. and treated with a solution of (2-bromophenyl)acetyl chloride (prepared from 0.65 g of the acid by treatment with thionyl chloride in benzene under reflux) in 7 ml of benzene. The mixture was stirred at 0° C. for 0.5 hour and then stored at 4° C. overnight. The solvents were removed by evaporation and the residue was re-evaporated with toluene to give a gum which was subsequently triturated with diethyl ether to yield a solid. This solid was taken up in 5 ml of methylene chloride/methanol (9:1) and chromatographed on a column of silica gel using methylene chloride/methanol (9:1) for the elution. The fractions containing the product were combined and evaporated. The residue was re-evaporated with ethanol and recrystallized from methanol to give 0.18 g of 5'-[2-(2-bromophenyl)-N-methylacetamido]-2',5'-dideoxy-5-ethyluridine of melting point 182°- 185° C.

Aufarbeitung

  1. waitstored at 4° C. overnight
  2. customThe solvents were removed by evaporation
  3. customthe residue was re-evaporated with toluene
  4. customto give a gum which
  5. customwas subsequently triturated with diethyl ether
  6. customto yield a solid
  7. customchromatographed on a column of silica gel
  8. washfor the elution
  9. additionThe fractions containing the product
  10. customevaporated
  11. customThe residue was re-evaporated with ethanol
  12. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-0a4a5431c02344ec9e064577c5674b63
Quelldatensatz
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05010060

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