4-Toluenesulfonyl chloride → N-(p-toluenesulphonyl)-L-alanyl-L-proline ethylamide

HRID 47048Notes

Reaction equation

HRID 47048 reaction equation
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH3:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 70602162L-alanyl-L-proline ethylamide hydrobromide

Product 1

HCID 53646160N-(p-toluenesulphonyl)-L-alanyl-L-proline ethylamideYield 33%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.0 g (0.0033 mol) of L-alanyl-L-proline ethylamide hydrobromide was dissolved in 20 ml of dry pyridine and 0.63 g (0.0033 mol) of p-toluenesulphonyl chloride was added. The mixture was stirred at room temperature for 1 hour and the pyridine was then removed by evaporation. The oily residue was dissolved in chloroform and the solution was washed with water, dried over magnesium sulphate and evaporated to an oil. This oil was dissolved in water and freeze-dried to yield 0.40 g (33%) of N-(p-toluenesulphonyl)-L-alanyl-L-proline ethylamide; [α]D20 =-90.7° (c=0.94% in water).

Workup

  1. customthe pyridine was then removed by evaporation
  2. dissolutionThe oily residue was dissolved in chloroform
  3. washthe solution was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to an oil
  6. dissolutionThis oil was dissolved in water
  7. customfreeze-dried

Sources & evidence

ORD record
ord-bc8d1b97509e42f6b38d35bbc920ab0f
Source dataset
uspto-grants-1979_11
Patent number
US04176116

Reaction notes

Loading…