Guanidine Hydrochloride → Zidovudine guanidine

HRID 273875

Reaction equation

HRID 273875 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].[OH-].[Na+].Cl.[NH2:23][C:24]([NH2:26])=[NH:25]>O>[NH2:25][C:24]([NH2:26])=[NH:23].[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 35370Zidovudine

Product 1

HCID 15817654Zidovudine guanidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

An analytical grade sample of the 3'-azido-3'-deoxythymidine guanidine salt was prepared by suspending pharmaceutical grade 3'-azido-3'-deoxythymidine (53.4 g) in water (250 mL) and adding 50% sodium hydroxide (17.6 g) to provide a mixture having a pH of 13.0. The mixture was then heated to 70° C. Thereafter, guanidine hydrochloride (23 g) was added as a solid and the mixture was heated to 97° C. to dissolve the emerging precipitate. The mixture was then set aside to cool and crystallize, and it was stirred for 16 hours. Thereafter, the crystals were filtered and washed with water and ethanol to yield 58.76 (90%) of white crystals. The crystals had a melting point of 210.9°-212° C.

Workup

  1. customto provide a mixture
  2. temperaturethe mixture was heated to 97° C.
  3. dissolutionto dissolve the emerging precipitate
  4. temperatureto cool
  5. customcrystallize
  6. filtrationThereafter, the crystals were filtered
  7. washwashed with water and ethanol

Sources & evidence

ORD record
ord-376241f84b824599b5aa7c407f3d20bb
Source dataset
uspto-grants-1995_02
Patent number
US05387677

Linked notes

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