Carbon tetrabromide → 5'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridine

HRID 232365

Reaktionsgleichung

Reaktionsgleichung von HRID 232365
[Cl:1][CH2:2][CH2:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14]O)[C@@H:11]([OH:12])[CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:39]=[N+:40]=[N-:41].[Li+].C(Br)(Br)(Br)Br>CN(C)C=O.CO>[N:39]([CH2:14][C@H:13]1[O:16][C@@H:9]([N:8]2[CH:17]=[C:4]([CH2:3][CH2:2][Cl:1])[C:5](=[O:19])[NH:6][C:7]2=[O:18])[CH2:10][C@@H:11]1[OH:12])=[N+:40]=[N-:41]

Komponenten

7

Edukt 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azideHCID 5148145-(2-Chloroethyl)-2'-deoxyuridine

Produkt 1

HCID 540023075'-Azido-2',5'-dideoxy-5-(2-chloroethyl)uridineAusbeute 31,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.4 g of 5-(2-chloroethyl)-2'-deoxyuridine and 1.3 g of triphenylphosphine were dissolved in 20 ml of dimethylformamide and stirred while 1.2 g of lithium azide were added to give a solution within 5 minutes at room temperature. 1.7 g of carbon tetrabromide were added portionwise during 5 minutes to give a hazy orange colored solution which was stirred at room temperature for 17 hours. 5 ml of methanol were added to give a clear solution. After 0.5 hour, the solvents were removed by evaporation under an oil pump vacuum to give a gum which was partitioned between 30 ml of ethyl acetate and 20 ml of water. The white solid which formed was removed by filtration to give 0.64 g of crude product of melting point 179°-182° C. (decomposition). This crude product was stirred with methanol and then removed by filtration to give 0.48 g of pure 5'-azido-2',5'-dideoxy-5-(2-chloroethyl)-uridine of melting point 197°-199° C. (decomposition).

Aufarbeitung

  1. additionwere added
  2. customto give a solution within 5 minutes at room temperature
  3. customto give a hazy orange colored solution which
  4. customto give a clear solution
  5. waitAfter 0.5 hour
  6. customthe solvents were removed by evaporation under an oil pump vacuum
  7. customto give a gum which
  8. customwas partitioned between 30 ml of ethyl acetate and 20 ml of water
  9. customThe white solid which formed
  10. customwas removed by filtration
  11. customto give 0.64 g of crude product of melting point 179°-182° C. (decomposition)
  12. customremoved by filtration

Quellen und Nachweise

ORD-Eintrag
ord-104589e5e70540d595c331276c191bfc
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851519

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