Sodium Azide → HCID 42598819, compound

HRID 875262Notes

Reaction equation

HRID 875262 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][C:17]2([OH:34])[C:21](=[O:22])[O:20][C@H:19]3[C:23]4[C@@:28]([CH3:31])([CH2:29][CH2:30][C:18]23[OH:33])[CH2:27][CH2:26][CH2:25][C:24]=4[CH3:32])(=O)=O)=CC=1>CN(C)C=O>[N:1]([CH2:16][C:17]1([OH:34])[C:21](=[O:22])[O:20][C@H:19]2[C:23]3[C@@:28]([CH3:31])([CH2:29][CH2:30][C:18]12[OH:33])[CH2:27][CH2:26][CH2:25][C:24]=3[CH3:32])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 42598818HCID 42598818, compound

Product 1

HCID 42598819HCID 42598819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium azide (32.5 mg, 0.5 mmol) was added to the solution of compound of example 5 (218 mg, 0.5 mmol) in dimethylformamide (DMF) (2 mL) and stirred at 50° C. under nitrogen atmosphere for 24 hours. The reaction mixture was concentrated, dried and was dissolved in water (25 mL) and was extracted with ethyl acetate (3×50 mL). The ethyl acetate layer was washed with water and brine and was dried over sodium sulfate. Solvent was removed and crude product was washed with petroleum ether, to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried
  3. dissolutionwas dissolved in water (25 mL)
  4. extractionwas extracted with ethyl acetate (3×50 mL)
  5. washThe ethyl acetate layer was washed with water and brine
  6. dry with materialwas dried over sodium sulfate
  7. customSolvent was removed
  8. washcrude product was washed with petroleum ether

Sources & evidence

ORD record
ord-195f28eed557431aa0e8727c9e013c06
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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