1-Hydroxybenzotriazole → t-Butyl[4-(5-cyano-2-propylaminophenylcarbamoyl)butyl]carbamate

HRID 2080723Notes

Reaction equation

HRID 2080723 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:44]=[CH:45][C:46]=1[NH:47][CH2:48][CH2:49][CH3:50])[C:42]#[N:43]>C(Cl)(Cl)Cl>[C:42]([C:41]1[CH:44]=[CH:45][C:46]([NH:47][CH2:48][CH2:49][CH3:50])=[C:39]([NH:38][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:15])[CH:40]=1)#[N:43]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223802993-Amino-4-(propylamino)benzonitrile

Product 1

HCID 21084519t-Butyl[4-(5-cyano-2-propylaminophenylcarbamoyl)butyl]carbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In chloroform (31 ml), 5-t-butoxycarbonylamino valeric acid (1.57 g), WSCI hydrochloride (1.98 g), and HOBt (1.39 g) were dissolved. Then, the solution was stirred at room temperature for 30 minutes. The solution was dropped in a chloroform solution (10 ml) containing the compound (1.18 g) obtained in Example 5-2. Then, the whole was stirred at room temperature for 12 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 sodium hydrogen carbonate solution, a saturated aqueous ammonium chloride solution, and a saturated saline solution, followed by drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate) to remove only highly-polar components, thereby obtaining a mixture (2.52 g) containing the subject compound as a yellow oily substance.

Workup

  1. stirringThen, the whole was stirred at room temperature for 12 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 sodium hydrogen carbonate solution
  6. dry with materialby drying with anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)
  10. customto remove only highly-polar components

Sources & evidence

ORD record
ord-1cfa19c5714544cfbb96f64860efe47b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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