Anisole → HCID 131723454, compound

HRID 2305305Notes

Reaction equation

HRID 2305305 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[NH:20](C(OC(C)(C)C)=O)[CH2:21][C:22]([OH:24])=[O:23].C1(OC)C=CC=CC=1.[ClH:40].O1CCOCC1>C(Cl)(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[NH2:20][CH2:21][C:22]([OH:24])=[O:23].[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([N:17]=[N+:18]=[N-:19])[CH2:11]2)[CH:3]=1.[ClH:40]

Participants

7

Reactant 4

HCID 7519AnisoleHCID 35370ZidovudineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 131723454HCID 131723454, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21754633chloroform N,N-dimethylformamideSolvent

Procedure

In a mixture of chloroform-DMF (1:1) was dissolved AZT (1.0 g), and to the solution were added under ice-cooling Boc-Gly-OH (1.32 g) and DMAP (0.46 g). The mixture was stirred overnight. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was successively washed with 5% citric acid solution, 5% sodium hydrogencarbonate solution and saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue was added n-hexane, and precipitates were filtered to give white powder. To the white powder were added anisole (0.25 ml) and 4N HCl/dioxane (5 ml), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and to the residue was added diethylether. Precipitates were filtered to give the title compound as white powder.

Workup

  1. additionto the solution were added under ice-
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was successively washed with 5% citric acid solution, 5% sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added n-hexane
  8. customprecipitates
  9. filtrationwere filtered
  10. customto give white powder
  11. stirringthe mixture was stirred at room temperature for 1 hour
  12. concentrationThe reaction solution was concentrated under reduced pressure
  13. additionto the residue was added diethylether
  14. customPrecipitates
  15. filtrationwere filtered

Sources & evidence

ORD record
ord-9bc368fa313a477a8000ce17616b45e3
Source dataset
uspto-grants-2002_08
Patent number
US06440946B1

Reaction notes

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