Ethylmorpholine → L-Pyroglutamyl-L-alanine amide

HRID 972704Notes

Reaction equation

HRID 972704 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.Cl.[NH2:22][C@H:23]([C:25]([NH2:27])=[O:26])[CH3:24].C(N1CCOCC1)C>CN(C)C=O>[NH:11]1[C:12](=[O:15])[CH2:13][CH2:14][C@H:10]1[C:9]([NH:22][C@H:23]([C:25]([NH2:27])=[O:26])[CH3:24])=[O:16]

Participants

5

Reactant 3

HCID 7525EthylmorpholineHCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 3035255Perchlorophenyl 5-oxo-L-prolinate

Product 1

HCID 22799701L-Pyroglutamyl-L-alanine amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.75 g (10 mmols) of L-pyroglutamic acid pentachlorophenyl ester were stirred in 40 ml of dimethyl formamide with 1.5 g (12 mmols) of L-alanine amide hydrochloride and 1.54 ml (12 mmols) of N-ethylmorpholine for 4 hours. The solvent was distilled off in vacuo. The residue was dissolved in methanol and the solution was stirred successively with strongly basic and strongly acid ion exchangers. The exchanger was removed by filtration and concentration to dryness followed. The residue was triturated with ethyl acetate, dissolved in a little ethanol and precipitated with petroleum ether in the form of a resin that solidified under petroleum ether. Yield: 1.2 g, chromatographically unfirom without sharp melting point.

Workup

  1. distillationThe solvent was distilled off in vacuo
  2. dissolutionThe residue was dissolved in methanol
  3. customThe exchanger was removed by filtration and concentration to dryness
  4. customThe residue was triturated with ethyl acetate
  5. dissolutiondissolved in a little ethanol
  6. customprecipitated with petroleum ether in the form of a resin that

Sources & evidence

ORD record
ord-2f893fed8cbd42a69a1dfa7f1fd2bf65
Source dataset
uspto-grants-1977_10
Patent number
US04053588

Reaction notes

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