Sodium Azide → HCID 178459235, compound

HRID 2368143Notes

Reaction equation

HRID 2368143 reaction equation
CS(O[CH:6]([CH3:29])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[O:16][C:17]3[CH:23]=[C:22]([O:24][CH2:25][CH:26]4[CH2:28][CH2:27]4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C>[N:30]([CH:6]([CH3:29])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[O:16][C:17]3[CH:23]=[C:22]([O:24][CH2:25][CH:26]4[CH2:28][CH2:27]4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1)=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178459236HCID 178459236, compound

Product 1

HCID 178459235HCID 178459235, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2-({trans-4-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]cyclohexyl}oxy)-1-methylethyl methanesulfonate 283 mg) and sodium azide (271 mg) in DMF (3 mL) was stirred at 60° C. overnight. The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (249 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate and water
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e2673fd632004d6a8ebfdd77b0c2b37b
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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