L-Glutamic Acid → p-Toluenesulfonic acid

HRID 1939848Notes

Reaction equation

HRID 1939848 reaction equation
COCCN(CCOC)C(=O)CCCCCO.N[C@H](C(O)=O)CCC(O)=O.O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[CH3:39][C:29]1[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 33032L-Glutamic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 21464486HCID 21464486, compound

Product 1

HCID 6101p-Toluenesulfonic acidYield 425.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N,N-Bis(2'-methoxyethyl)-6-hydroxyhexanamide (10.0 g, Example 5), L-glutamic Acid (2.97 g) and p-toluenesulfonic acid monohydrate (4.03 g) in toluene (30 mL) was refluxed under nitrogen. Water was separated from the distillate in a Barrett distilling receiver. When the theoretical amount of water (1.1 g) was collected, the heating was stopped and the toluene removed in vacuo on a rotary evaporator. The product was obtained as its p-toluenesulfonate salt as a brown oil (15.51 g).

Workup

  1. temperaturewas refluxed under nitrogen
  2. customWater was separated from the distillate in a Barrett
  3. distillationdistilling receiver
  4. customWhen the theoretical amount of water (1.1 g) was collected
  5. customthe toluene removed in vacuo on a rotary evaporator

Sources & evidence

ORD record
ord-6d1a8316dae9464aa547c5f7bcf95fde
Source dataset
uspto-grants-1997_12
Patent number
US05698016

Reaction notes

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