Sodium Azide → HCID 86594308, compound

HRID 751175Notes

Reaction equation

HRID 751175 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([N:10]2[CH2:14][CH:13]3[C@@H:15](CS([O-])(=O)=O)[CH2:16][CH2:17][N:12]3[C:11]2=[O:23])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([N:10]2[CH2:14][C@@H:13]3[C@H:15]([N:25]=[N+:26]=[N-:27])[CH2:16][CH2:17][N:12]3[C:11]2=[O:23])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86594309HCID 86594309, compound

Product 1

HCID 86594308HCID 86594308, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of compound 90A (400 mg, 1.18 mmol) and sodium azide (309 mg, 4.75 mmol) in anhydrous DMF (3.2 mL) was placed in a pre-heated bath (75° C.) and stirred at 75° C. for 3 h. The solution was cooled, quenched with H2O (6.0 mL) and extracted with EtOAc (2×80 mL). The organic phase was washed with H2O (6.0 mL), brine (6.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The syrup was chromatographed (silica gel; CH2Cl2/CH3OH gradient) to yield the title compound (339.3 mg, 90.8%) as a white solid foam from CH2Cl2/Hexane. HPLC: 97.7% at 2.22 min (retention time) (Conditions: YMC S-5 C-18 (4.6×50 mm), eluting with 0-100% B, 4 min gradient. (A=90% H2O—10% CH3CN—0.1% TFA and B=10% H2O—90% CH3CN—0.1% TFA); Flow rate at 4 mL/min. UV detection at 220 nm. MS (ES+): m/z 317 [M+H]+.

Workup

  1. temperatureThe solution was cooled
  2. customquenched with H2O (6.0 mL)
  3. extractionextracted with EtOAc (2×80 mL)
  4. washThe organic phase was washed with H2O (6.0 mL), brine (6.0 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe syrup was chromatographed (silica gel; CH2Cl2/CH3OH gradient)

Sources & evidence

ORD record
ord-b1de9129a55149c991e0f3ea831d2a50
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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