Hydrochloric Acid → Zidovudine

HRID 440428

Reaction equation

HRID 440428 reaction equation
Cl.[CH3:2][C:3]1[C:9](=[O:10])[NH:8][C:6](=[O:7])[N:5]([C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)[CH:4]=1.NC(N)=N>O>[CH3:2][C:3]1[C:9](=[O:10])[NH:8][C:6](=[O:7])[N:5]([C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 15817654Zidovudine guanidine

Product 1

HCID 35370ZidovudineYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of water (90 mL) and 32% hydrochloric acid (31.4 g) was heated at 75° C. Zidovudine-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 zidovudine 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 zidovudine-guanidine complex suitable for recycling (i.e. acidification).

Workup

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

Sources & evidence

ORD record
ord-002c043efee7446bbd90f4ece77e4284
Source dataset
uspto-grants-1996_05
Patent number
US05519129

Linked notes

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