Benzene → HCID 56828181, compound

HRID 1494499Notes

Reaction equation

HRID 1494499 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1.C1C=CC=CC=1>O>[C:20]1([CH3:30])[CH:21]=[CH:22][C:23]([S:26]([OH:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1.[C:20]1([CH3:30])[CH:21]=[CH:22][C:23]([S:26]([OH:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1.[CH2:11]([O:9][C:8](=[O:10])[C@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][NH2:7])[NH2:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 244Benzyl AlcoholHCID 5962L-LysineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 56828181HCID 56828181, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g of L-lysine (20.5·10-2 mole) and 70 ml of distilled benzyl alcohol (67.6·10-2 mole) are introduced into an extractor of the Dean-Stark type; 88.5 g of paratoluene sulfonic acid monohydrate (46.5·10-2 mole) and 300 ml of benzene are added. The mixture is heated at reflux until all of the water formed in the reaction has been removed. The solution is transferred to a beaker to which 100 ml of methanol are added. The salt is precipitated by the addition of 500 ml of ethyl ether at room temperature. The precipitate is taken up by warming in 300 ml of methanol and reprecipitated by ethyl ether. 100 g of the N,N'-ditosylate of L-lysine benzyl ester are recovered; yield=84%, M.P.=163° C.

Workup

  1. temperatureThe mixture is heated
  2. customformed in the reaction
  3. customhas been removed
  4. additionare added
  5. customThe salt is precipitated by the addition of 500 ml of ethyl ether at room temperature
  6. temperatureby warming in 300 ml of methanol
  7. customreprecipitated by ethyl ether
  8. custom100 g of the N,N'-ditosylate of L-lysine benzyl ester are recovered

Sources & evidence

ORD record
ord-f902a0a049344f20a73369388a340e1b
Source dataset
uspto-grants-1991_06
Patent number
US05026821

Reaction notes

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