2-Methylpentane → HCID 57951197, compound

HRID 1919812Notes

Reaction equation

HRID 1919812 reaction equation
[N-]=[N+:2]=[N-:3].[Na+].CCCC(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.ClC1C=CC(C([CH:33]2[CH2:37][CH:36]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[CH:39]=3)[N:35]([C:45]3[CH:50]=[CH:49][C:48]([O:51][C:52]([F:55])([F:54])[F:53])=[CH:47][CH:46]=3)[C:34]2=[O:56])=O)=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C(#N)C.C(OCC)(=O)C>[N+:2](=[C:33]1[CH2:37][C@H:36]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[CH:39]=2)[N:35]([C:45]2[CH:46]=[CH:47][C:48]([O:51][C:52]([F:55])([F:53])[F:54])=[CH:49][CH:50]=2)[C:34]1=[O:56])=[N-:3]

Participants

9

Reactant 4

HCID 78922-MethylpentaneHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 76673623HCID 76673623, compound

Product 1

HCID 57951197HCID 57951197, compoundYield 70.2%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Dissolve sodium azide (2.6 g, 40 mmol) and tetrabutylammonium bromide (260 mg, 0.8 mmol) in 2N sodium hydroxide solution (50 mL), add isohexane (50 mL) and stir while cooling in an ice-water bath. Add trifluoromethanesulfonic anhydride (2.0 mL, approx 12 mmol) dropwise, stir for 10 minutes with cooling. Dissolve (5R)-(3-(4-chlorobenzoyl-5-(3-fluoro-phenyl)-1-(4-trifluoromethoxy-phenyl)-pyrrolidin-2-one (1.1 g, 2.3 mmol) in acetonitrile (30 mL), add to the reaction mixture and stir vigorously for 30 minutes. Dilute the reaction mixture with ethyl acetate (150 mL) and wash with brine. Collect the organic phase, dry over anhydrous magnesium sulfate, evaporate and purify on a silica gel column (isohexane-ethyl acetate) to give the titled compound (590 mg, 70% yield) MS (m/z): 366 (M+1).

Workup

  1. temperaturewhile cooling in an ice-water bath
  2. temperaturewith cooling
  3. additionadd to the reaction mixture
  4. stirringstir vigorously for 30 minutes
  5. washwash with brine
  6. customCollect the organic phase
  7. dry with materialdry over anhydrous magnesium sulfate
  8. customevaporate
  9. custompurify on a silica gel column (isohexane-ethyl acetate)

Sources & evidence

ORD record
ord-6fc05028b8704383890f417f180941c4
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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