Hydrochloric Acid → Zidovudine

HRID 273874

Reaction equation

HRID 273874 reaction equation
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]

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. 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).

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-ec9f88dd80494d4ab25075246d7f3944
Source dataset
uspto-grants-1995_02
Patent number
US05387677

Linked notes

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