Hydrochloric Acid → Zidovudine

HRID 273874

Reaktionsgleichung

Reaktionsgleichung von HRID 273874
Cl.[N:2]([C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[CH:20]=[C:18]([CH3:19])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:6]1)=[N+:3]=[N-:4].NC(N)=N>O>[N:2]([C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:12]2[CH:20]=[C:18]([CH3:19])[C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH2:6]1)=[N+:3]=[N-:4]

Komponenten

4

Edukt 2

HCID 313Hydrochloric Acid2×HCID 15817654Zidovudine guanidine

Produkt 1

HCID 35370ZidovudineAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of water (90 mL) and 32% hydrochloric acid (31.4 g) was heated at 75° C. 3'-azido-3'-deoxythymidine-guanidine complex (90 g) from Example 1 was added in portions to the aqueous solution and when the addition was completed the pH was 7.56. Thereafter, the pH was adjusted to 1.0 by further addition of 32% hydrochloric acid. The mixture was cooled and crystals formed spontaneously. After several hours the crystals were filtered to yield 61.64 g of crude 3'-azido-3'-deoxythymidine suitable for final purification. 50% caustic (22 g) was added to the mother liquor and a precipitate formed. After 30 minutes the precipitate was filtered to yield 7.99 g 3'-azido-3'-deoxythymidine-guanidine complex suitable for recycling (i.e. acidification).

Aufarbeitung

  1. additionthe addition
  2. temperatureThe mixture was cooled
  3. customcrystals formed spontaneously
  4. filtrationAfter several hours the crystals were filtered

Quellen und Nachweise

ORD-Eintrag
ord-ec9f88dd80494d4ab25075246d7f3944
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387677

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