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

HRID 1733661Notes

Reaction equation

HRID 1733661 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c566f2e7878543db84dc27409eeda8cb
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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