Hydrochloric Acid → N-[N-(2-pyridyl)ethyl-N-methylaminocarbonyl]-L-phenylalanine benzyl ester

HRID 2396150Notes

Reaction equation

HRID 2396150 reaction equation
Cl.C(O[C:7]([N:9]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH3:10])=[O:8])(C)(C)C.[CH2:19]([O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.ClC(OC(Cl)=O)(Cl)Cl>C(OCC)(=O)C>[CH2:19]([O:26][C:27](=[O:37])[C@H:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:29][C:7]([N:9]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH3:10])=[O:8])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10426DiphosgeneHCID 736312Benzyl 3-phenyl-L-alaninateHCID 18988032HCID 18988032, compound

Product 1

HCID 15018179N-[N-(2-pyridyl)ethyl-N-methylaminocarbonyl]-L-phenylalanine benzyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4N-hydrogen chloride in ethyl acetate (5 ml) was added to 2-[2-(N-t-butoxycarbonyl-N-methylamino)ethyl]pyridine at 0° C. The solution was stirred at 0° C. for 1 hour and concentrated under reduced pressure. The residue was dissolved in methylene chloride (10 ml). Triethylamine (304 mg) and (1S)-1-benzyloxycarbonyl-2-phenylethyl isocyanate (281 mg) prepared by reacting L-phenylalanine benzyl ester with trichloromethylchloroformate was added to this solution at 0° C. The solution was stirred at the same temperature for 1 hour and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with 10% citric acid aqueous solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution successively, dried over magnesium sulfate, and concentrated under reduced pressure to give N-[N-(2-pyridyl)ethyl-N-methylaminocarbonyl]-L-phenylalanine benzyl ester (400 mg) as an oil. Rf: 0.50 ( chloroform:methanol, 20: 1, V/V)

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride (10 ml)
  3. customTriethylamine (304 mg) and (1S)-1-benzyloxycarbonyl-2-phenylethyl isocyanate (281 mg) prepared
  4. additionwas added to this solution at 0° C
  5. stirringThe solution was stirred at the same temperature for 1 hour
  6. customthe solvent was evaporated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washthe solution was washed with 10% citric acid aqueous solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution successively
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-318d5dee4a70480b9809ef037d7f296b
Source dataset
uspto-grants-1996_02
Patent number
US05491132

Reaction notes

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