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Chemical Structure| 46741-65-5 Chemical Structure| 46741-65-5

Structure of 46741-65-5

Chemical Structure| 46741-65-5

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Product Details of [ 46741-65-5 ]

CAS No. :46741-65-5
Formula : C13H19NO2
M.W : 221.30
SMILES Code : CC(C)C[C@@H](N)C(OCC1=CC=CC=C1)=O

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Application In Synthesis of [ 46741-65-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 46741-65-5 ]

[ 46741-65-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 46741-65-5 ]
  • [ 59969-65-2 ]
  • [ 62058-27-9 ]
  • 2
  • [ 17664-93-6 ]
  • [ 46741-65-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; Preparation of 3-[(1R)-1-(benzyloxycarbonyl)-3-methylbutyl]amino}-1-propanesulfonic acid (Compound HI); D-Leucine benzylester p-tosylate (2.5 g, 6.3 mmol) was treated with an aqueous solution of K2CO3 (30 mL). The mixture was extracted with EtOAc (3×30 mL). The organic extracts were separated, combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To a solution of D-Leucine benzylester (6.3 mmol) in acetonitrile (9 mL) and MeOH (3 mL) was added 1,3-propane sultone (691 mg, 5.7 mmol). The solution was stirred at reflux for 2.5 hours. The reaction mixture was cooled to room temperature. The solid material was filtered and washed with aconitrile (2×20 mL). The solid was dissolved in 20% water/EtOH (75 mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure and dried in vacuo, affording the title compound (960 mg, 49%). 1H NMR (D2O, 500 MHz) delta ppm 7.52 (m, 5H), 5.41 (d, 1H, J=12.2 Hz), 5.35 (d, 1H, J=12.2 Hz), 4.16 (m, 1H), 3.22 (m, 2H), 2.97 (t, 2H, J=6.8 Hz), 2.16 (m, 2H), 1.88 (m, 1H), 1.79 (m, 1H), 1.76 (m, 1H), 0.94 (d, 6H, J=3.9 Hz). 13C (DMSO, 125 MHz) delta ppm 169.60, 135.62, 129.24, 129.21, 129.11, 68.08, 58.09, 49.87, 46.48, 24.77, 23.50, 22.50, 22.04. [alpha]D=-2.1 (c=0.00095 in water), ES-MS 344 (M+1).
  • 3
  • [ 46741-65-5 ]
  • [ 59969-65-2 ]
  • bestatin [ No CAS ]
 

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