Ammonium Chloride → HCID 12085842, compound

HRID 1357493Notes

Reaction equation

HRID 1357493 reaction equation
[CH2:1]([C@@H:4]1[C@H:10]2[C@H:8]([O:9]2)[CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[CH2:5]1)[CH:2]=[CH2:3].[N-:15]=[N+:16]=[N-:17].[Na+].[NH4+].[Cl-]>CO.O>[CH2:1]([C@H:4]1[CH2:5][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C@H:8]([N:15]=[N+:16]=[N-:17])[C@H:10]1[OH:9])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12085841HCID 12085841, compound

Product 1

HCID 12085842HCID 12085842, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of Example 1I, sodium azide (2.8 g, 43.1 mmol) and NH4Cl (1.0 g, 18.8 mL) in methanol (30 mL) and H2O (10 mL) was refluxed for 5 hours, diluted with H2O and extracted with ethyl acetate. The combined ethyl acetate layers were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (1/1) to afford 1.4 g (67% over steps I and J) of the desired product as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-8c60780df3eb4332b7b7518793e0a283
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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