Sodium Bicarbonate → Zidovudine

HRID 1649883Notes

Reaction equation

HRID 1649883 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10]C(OC)=O)[O:7][C@@H:6]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:5]1)=[N+:2]=[N-:3].C(=O)(O)[O-].[Na+]>CO>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18639108HCID 18639108, compound

Product 1

HCID 35370ZidovudineYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3'-azido-3'-deoxy-5'-O-(methoxycarbonyl)thymidine (2.50 g, 7.68 mmoles) from Example A14 and sodium bicarbonate (0.50 g) was heated 2.5 h at reflux in methanol (75 mL). The solvent was removed by rotary evaporation and the residual semi-solid was triturated with cold 5% aq. sodium bicarbonate (50 mL). The resulting solid was collected by filtration and dried in a vacuum oven at 55° C. for 17 h affording 1.71 g (83.4%) of 3'-azido-3'-deoxythymidine: mp 119°-121° C.; 1H NMR (DMSO-d6) δ1.79 (d, J=1.04 Hz, 3H C-5 CH3), 2.10-2.56 (m, 2H, C-2'H), 3.31-3.92 (m, 3H, C-3' and C-5'H), 4.40 (m, 1H, C-4'H), 5.19 (t, J=5.22 Hz, 1H, OH), 6.11 (t, J=6.46 Hz, 1H, C-1'H), 7.68 (q, J=1.04, 1H, C-6H) and 10.65 (broad, 1H, NH); TLC Rf =0.35, silica gel, CHCl3 :CH3OH/90:10.

Workup

  1. temperaturewas heated 2.5 h
  2. customThe solvent was removed by rotary evaporation
  3. customthe residual semi-solid was triturated with cold 5% aq. sodium bicarbonate (50 mL)
  4. filtrationThe resulting solid was collected by filtration
  5. customdried in a vacuum oven at 55° C. for 17 h

Sources & evidence

ORD record
ord-eff0b99e59524fcea18d9cd00ca4314e
Source dataset
uspto-grants-1990_05
Patent number
US04921950

Reaction notes

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