4-Toluenesulfonyl chloride → HCID 131712270, compound

HRID 1680777Notes

Reaction equation

HRID 1680777 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:18]([OH:20])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].C([O-])(O)=O.[Na+].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>O.O1CCOCC1>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:18]([OH:20])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][N:15]([S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=2)(=[O:35])=[O:34])[CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178511824HCID 178511824, compound

Product 1

HCID 131712270HCID 131712270, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3 g (10 mmols) of Glu-His-OH and 2.3 g of NaHCO3 are dissolved in 20 ml of water and, while stirring at room temperature, a solution of 2.1 g (10% excess) of p-toluene sulfochloride in about 10 ml of dioxane is slowly added drop by drop. When the addition is terminated, stirring of the mixture is continued for a further hour, whereupon it is extracted twice with ether. The aqueous phase is acidified to pH 2 with 2 N HCl and the precipitate is filtered off with suction. It is washed with water and the filer residue is dried over P2O5 under reduced pressure. Yield 2.2 g.

Workup

  1. additionWhen the addition
  2. customis terminated
  3. stirringstirring of the mixture
  4. waitis continued for a further hour, whereupon it
  5. extractionis extracted twice with ether
  6. filtrationthe precipitate is filtered off with suction
  7. washIt is washed with water
  8. dry with materialthe filer residue is dried over P2O5 under reduced pressure

Sources & evidence

ORD record
ord-a1f7321d2c204756a88dd2f7977701ef
Source dataset
uspto-grants-1981_06
Patent number
US04275001

Reaction notes

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