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

HRID 495038

反応式

HRID 495038 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8a0bf6eb5ba24dd58306be6651ae0b9a
出典データセット
uspto-grants-2009_05
特許番号
US07538215B2

関連ノート

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