Butylamine → L-pyroglutamic acid n-butyl amide

HRID 972702Notes

Reaction equation

HRID 972702 reaction equation
ClC1C(O[C:9](=[O:16])[C@@H:10]2[CH2:14][CH2:13][C:12](=[O:15])[NH:11]2)=C(Cl)C(Cl)=C(Cl)C=1Cl.[CH2:21]([NH2:25])[CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH2:21]([NH:25][C:9](=[O:16])[C@@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11]1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 3035255Perchlorophenyl 5-oxo-L-prolinate

Product 1

HCID 15486634L-pyroglutamic acid n-butyl amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.5 g (20 mmols) of L-pyroglutamic acid pentachlorophenyl ester and 1.75 g (2.4 mmols) of n-butyl amine were stirred in 100 ml of tetrahydrofurane for 5 hours. The solvent was distilled off. The residue was dissolved in methanol and treatment with strongly basic and then with strongly acidic ion exchangers followed. After filtration, methanol was distilled off. The oily residue was dissolved and precipitated with petroleum ether. After a prolonged period of time, the product, which has precipitated in oily form, became solid. It was filtered off, washed with petroleum ether and dried under vacuum.

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionThe residue was dissolved in methanol
  3. filtrationAfter filtration, methanol
  4. distillationwas distilled off
  5. dissolutionThe oily residue was dissolved
  6. customprecipitated with petroleum ether
  7. waitAfter a prolonged period of time
  8. customthe product, which has precipitated in oily form
  9. filtrationIt was filtered off
  10. washwashed with petroleum ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-60b333c5806a4bc5b3766b6eb2f62682
Source dataset
uspto-grants-1977_10
Patent number
US04053588

Reaction notes

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