Hydrochloric Acid → HCID 59552587, compound

HRID 1803824Notes

Reaction equation

HRID 1803824 reaction equation
C(OC([NH:8][C@@H:9]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33]C2CCCCO2)=[CH:26][CH:25]=1)[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.Cl.[N-:41]=[N+:42]=[N-].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([O-])(O)=O.[Na+]>O1CCOCC1.N1C=CC=CC=1.O>[N:8]([C@@H:9]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][OH:33])=[CH:26][CH:25]=1)[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11])=[N+:41]=[N-:42]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 59552404HCID 59552404, compound

Product 1

HCID 59552587HCID 59552587, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
23 °C

Procedure

To a stirring solution of the amide 143 (8.8 g, 16 mmol) in dioxane (20 mL) at 23° C. was added a solution of 4 M HCl in dioxane (320 mL). The mixture was stirred for 9 h and concentrated in vacuo to afford a crude, clear, viscous pale-yellow oil. A slurry of NaN3 (1.56 g, 24 mmol) in pyridine (25 mL) was then cooled to 0° C. and trifluoromethanesulfonic anhydride (4 mL, 24 mmol) was added dropwise before allowing the mixture to warm to 23° C. and stir for 3 h. A solution of the amine hydrochloride (6.4 g, 16 mmol) in H2O (11 mL) was then added followed by CuSO4.5H2O (600 mg, 2.4 mmol). The combined mixture was allowed to stir at 23° C. overnight. An aqueous saturated solution of NaHCO3 was then added and the organic layer was extracted 3×EtOAc. The combined organic extracts were washed 1×10% CuSO4, 2×1 M HCl, 1×brine, and dried over MgSO4. Solvents were removed in vacuo and the crude residue purified by flash chromatgraphy on silica gel using hexanes/ethyl actetate on a Biotage purification system yielding the azide 144 as a colorless, viscous oil (3.3 g, 53%).

Workup

  1. concentrationconcentrated in vacuo
  2. customto afford a crude
  3. stirringstir for 3 h
  4. stirringto stir at 23° C. overnight
  5. extractionthe organic layer was extracted 3×EtOAc
  6. washThe combined organic extracts were washed 1×10% CuSO4, 2×1 M HCl, 1×brine
  7. dry with materialdried over MgSO4
  8. customSolvents were removed in vacuo
  9. customthe crude residue purified by flash chromatgraphy on silica gel
  10. customon a Biotage purification system

Sources & evidence

ORD record
ord-174aad1bcb6c4f2c95bb8fb4ca40bc5e
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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