1-Hydroxybenzotriazole → HCID 66941905, compound

HRID 2080746Notes

Reaction equation

HRID 2080746 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][C:48]=1[NH2:49])[C:42]([O:44][CH3:45])=[O:43]>CN(C=O)C>[CH3:45][O:44][C:42](=[O:43])[C:41]1[CH:46]=[CH:47][C:48]([NH2:49])=[C:39]([NH:38][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:40]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66941905HCID 66941905, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (20 ml), 5-t-butoxycarbonylamino valeric acid (manufactured by Aldrich Corporation) (1.45 g), WSCI hydrochloride (1.74 g), and HOBt (1.25 g) were dissolved and the whole was stirred for 15 minutes. Then, the solution was added with methyl 3,4-diaminobenzoate (1.00 g) and stirred at room temperature for 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and then washed with a saturated aqueous ammonium chloride solution and a 1 mol/l sodium hydroxide aqueous solution. Subsequently, the resultant was subjected to extraction with chloroform and the extract was then washed with a saturated saline solution, followed by drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.46 g).

Workup

  1. stirringstirred at room temperature for 4 hours
  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. extractionSubsequently, the resultant was subjected to extraction with chloroform
  7. washthe extract was then washed with a saturated saline solution
  8. dry with materialby drying with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-cfe4fb7eeb1c4fffac73240f7df8e47d
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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