Sodium Carbonate → N-{4-chloro-6-(N,N-dihexylamino)-1,3,5-triazin-2-yl}phenylalanine ethyl ester

HRID 495038

Reaction equation

HRID 495038 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[Cl:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([N:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C.O>[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:7][C:21]1[N:22]=[C:17]([Cl:16])[N:18]=[C:19]([N:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[N:20]=1)[CH3:3]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 105206134,6-Dichloro-N,N-dihexyl-1,3,5-triazin-2-amine

Product 1

HCID 57120797N-{4-chloro-6-(N,N-dihexylamino)-1,3,5-triazin-2-yl}phenylalanine ethyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

L-phenylalanine ethyl ester hydrochloride (1.0 g, 4.4 mmol) was added to a mixture of 2,4-dichloro-6-dihexylamino-1,3,5-triazine (1.5 g, 4.5 mmol) and sodium carbonate (0.92 g, 8.7 mmol) in acetonitrile (40 mL). The reaction mixture was heated to reflux for 16 h and then allowed to col to ambient temperature. The mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by flash column chromatography through silica gel (elution with chloroform) to afford N-{4-chloro-6-(N,N-dihexylamino)-1,3,5-triazin-2-yl}phenylalanine ethyl ester. Anal. Calcd. for C26H40ClN5O2: C, 63.72; H, 8.23; N 14.29. Found: C, 63.67; H, 8.06; N, 14.24.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. customto col to ambient temperature
  4. customThe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash column chromatography through silica gel (elution with chloroform)

Sources & evidence

ORD record
ord-8a0bf6eb5ba24dd58306be6651ae0b9a
Source dataset
uspto-grants-2009_05
Patent number
US07538215B2

Linked notes

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