Dimethylformamide → HCID 178524097, compound

HRID 1788407Notes

Reaction equation

HRID 1788407 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC[N:25]([CH:29](C)C)[CH:26]([CH3:28])C.C([O:34][C:35](=[O:51])[C:36]1[CH:41]=[CH:40][C:39]([NH:42][C@H:43]2[CH2:48][CH2:47][C@H:46]([OH:49])[CH2:45][CH2:44]2)=[C:38]([NH2:50])[CH:37]=1)C.C[N:53]([CH:55]=O)[CH3:54]>>[OH:49][C@H:46]1[CH2:45][CH2:44][C@H:43]([N:42]2[C:39]3[CH:40]=[CH:41][C:36]([C:35]([OH:34])=[O:51])=[CH:37][C:38]=3[N:50]=[C:41]2[C:36]2[CH:35]=[C:54]3[C:26](=[CH:28][CH:37]=2)[N:25]=[C:29]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:55]=[N:53]3)[CH2:48][CH2:47]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178469030HCID 178469030, compound

Product 1

HCID 178524097HCID 178524097, compound

Procedure

Compound 36A Y=Phenyl, (200 mg, 0.8 mmol) was activated in 8 mL DMF with TBTU (282 mg, 0.88 mmol) and DIEA (0.285 mL, 1.6 mmol) for 30 minutes at room temperature. This solution was then added to Compound 579b (265 mg, 0.95 mmol) and stirred at ambient temperature for 20 hours. The reaction was concentrated to a residue in-vacuo and then dissolved in acetic acid (20 mL) and refluxed overnight. In the morning, the acetic acid was removed in-vacuo and the crude residue dissolved in a mixture of THF (20 mL), methanol (16 mL) and 2 M NaOH (4 mL) and the solution heated at 60 C. overnight. The solution was then concentrated in-vacuo to an aqueous solution and concentrated HCl added until the pH was 5. The resulting precipitate was filtered, washed with water and purified using RP-HPLC column to give the pure title compound.

Workup

  1. concentrationThe reaction was concentrated to a residue in-vacuo
  2. dissolutiondissolved in acetic acid (20 mL)
  3. temperaturerefluxed overnight
  4. customIn the morning, the acetic acid was removed in-vacuo
  5. dissolutionthe crude residue dissolved in a mixture of THF (20 mL), methanol (16 mL) and 2 M NaOH (4 mL)
  6. temperaturethe solution heated at 60 C
  7. customovernight
  8. concentrationThe solution was then concentrated in-vacuo to an aqueous solution and concentrated HCl
  9. additionadded until the pH was 5
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with water
  12. custompurified

Sources & evidence

ORD record
ord-28c8ed27750a429a900e0c2e79d0c12a
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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