1-Hydroxybenzotriazole → HCID 67103843, compound

HRID 2080819Notes

Reaction equation

HRID 2080819 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][CH3:15])C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCC[N:24]([CH3:26])C.Cl.[CH:28]1[CH:29]=[CH:30][C:31]2[N:36](O)N=[N:34][C:32]=2[CH:33]=1.C(Cl)(Cl)Cl.CN([CH:45]=[O:46])C>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:13][CH2:14][CH2:15][C:45](=[O:46])[NH:34][C:32]1[CH:33]=[C:28]([C:26]#[N:24])[CH:29]=[CH:30][C:31]=1[NH2:36])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 3024332-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21754633chloroform N,N-dimethylformamide

Product 1

HCID 67103843HCID 67103843, compound

Procedure

In chloroform/DMF (60 ml/30 ml), t-butoxycarbonylamino valeric acid (3.91 g), WSCI hydrochloride (4.02 g), and HOBt (2.82 g) were dissolved and the whole was stirred for 1 hour. The solution was added with the compound (2.32 g) obtained in Example 39-2 and the whole was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (4.06 g) as a white solid.

Workup

  1. stirringthe whole was stirred overnight at room temperature
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a saturated aqueous ammonium chloride solution
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution, and then dried with anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-87001aa7b6354d869e22167b0e516a47
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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