Tetra-n-butylammonium tribromide → HCID 178462124, compound

HRID 1944760Notes

Reaction equation

HRID 1944760 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[F:55][C:56]1[CH:61]=[CH:60][C:59]([C@H:62]([NH:64][C:65]([C@H:67]2[CH2:72][CH2:71][C@H:70]([NH:73][S:74]([C:77]3[CH:82]=[CH:81][C:80]([C:83](=[O:85])[CH3:84])=[CH:79][CH:78]=3)(=[O:76])=[O:75])[CH2:69][CH2:68]2)=[O:66])[CH3:63])=[CH:58][CH:57]=1>C(Cl)Cl.CO>[F:55][C:56]1[CH:61]=[CH:60][C:59]([C@H:62]([NH:64][C:65]([C@H:67]2[CH2:68][CH2:69][C@H:70]([NH:73][S:74]([C:77]3[CH:78]=[CH:79][C:80]([C:83](=[O:85])[CH2:84][Br:1])=[CH:81][CH:82]=3)(=[O:75])=[O:76])[CH2:71][CH2:72]2)=[O:66])[CH3:63])=[CH:58][CH:57]=1

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 178466872HCID 178466872, compound

Product 1

HCID 178462124HCID 178462124, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Tetrabutylammonium-tribromide (216 mg, 0.447 mmol) was added to solution of trans-4-(4-acetyl-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 104, 194 mg, 0.434 mmol) in DCM/MeOH (2/1, 1.45 ml) at room temperature. The reaction was stirred 16-40 hours, then concentrated and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated to crude product which was chromatographed on a Biotage 40S column using ethyl acetate/heptane as the eluent to give the title compound (122 mg, 0.232 mmol).

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated to crude product which
  5. customwas chromatographed on a Biotage 40S column

Sources & evidence

ORD record
ord-845588f71fc144239777f1473db2af39
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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