Hydrochloric Acid → Zidovudine

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence