Triethylamine → (S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate

HRID 1733661

反応式

HRID 1733661 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:31])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.CS(ON1C2C=CC=CC=2N=N1)(=O)=O.C(OCC)(=O)C>C(Cl)(Cl)Cl.O>[CH2:12]([O:19][C:20](=[O:31])[C@H:21]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)[NH2:22])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 104540O-benzyl-L-tyrosine toluene-p-sulphonateHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

生成物 1

HCID 104541(S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate収率 147.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

Nα -Tert.-butoxycarbonyl-NG -nitro-L-arginine (1.60 g) and L-tyrosine benzyl ester p-toluenesulfonate (2.22 g) are dissolved in anhydrous chloroform (20 ml), and thereto are added triethylamine (1.40 ml) and further 1-methanesulfonyloxy-1,2,3-benzotriazole (1.05 g) and the mixture is stirred at room temperature for 20 hours. After the reaction, to the reaction mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed with water, a saturated aqueous sodium hydrogen carbonate, water, an aqueous citric acid solution and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off, and the resulting residue is dissolved in chloroform, subjected to chromatography by using silica gel (20 g) and eluted with chloroform to give amorphous powder of N-(Nα -tert.-butoxycarbonyl-NG -nitro-L-arginyl)-L-tyrosine benzyl ester (2.0 g).

後処理

  1. customAfter the reaction
  2. customThe ethyl acetate layer is separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate, water, an aqueous citric acid solution and water in order and then dried over anhydrous magnesium sulfate
  5. customAfter drying
  6. distillationthe solvent is distilled off
  7. dissolutionthe resulting residue is dissolved in chloroform
  8. washeluted with chloroform

出典と根拠

ORDレコード
ord-c566f2e7878543db84dc27409eeda8cb
出典データセット
uspto-grants-1980_12
特許番号
US04242507

関連ノート

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