Hexylamine → L-pyroglutamic acid n-hexyl amide

HRID 972703Notes

Reaction equation

HRID 972703 reaction equation
[CH2:1]([NH2:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].ClC1C=C(Cl)C(Cl)=CC=1[O:17][C:18](=O)[C@@H:19]1[CH2:23][CH2:22][C:21](=[O:24])[NH:20]1>CN(C)C=O>[CH2:1]([NH:7][C:18](=[O:17])[C@@H:19]1[CH2:23][CH2:22][C:21](=[O:24])[NH:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 8102HexylamineHCID 1111082,4,5-Trichlorophenyl 5-oxo-L-prolinate

Product 1

HCID 54158437L-pyroglutamic acid n-hexyl amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 ml of n-hexyl amine were added at 0° C. to a solution of 3.1 g of L-pyroglutamic acid 2,4,5-trichlorophenyl ester in 10 ml of dimethyl formamide and the solution was left at room temperature for 20 hours. The solvent was removed by distillation in vacuo at room temperature. The residue was taken up in 90% aqueous methanol, and the solution was filtered successively through 200 ml each of Levatit S 100(H+ -form)and Serdolit Blau (OH- -form). The ion exchanger columns were washed with 200 ml of 90% methanol and the combined eluate and washing solution were concentrated in vacuo. The L-pyroglutamic acid n-hexyl amide obtained as a colorless solid was recrystallized from ethyl acetate.

Workup

  1. customThe solvent was removed by distillation in vacuo at room temperature
  2. filtrationthe solution was filtered successively through 200 ml each of Levatit S 100(H+ -form)and Serdolit Blau (OH- -form)
  3. washThe ion exchanger columns were washed with 200 ml of 90% methanol
  4. washthe combined eluate and washing solution
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-9605a953e7554adc979b013a2dfb99e5
Source dataset
uspto-grants-1977_10
Patent number
US04053588

Reaction notes

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