Ethylmorpholine → L-Pyroglutamyl-4-aminobutyric acid amide

HRID 972707Notes

Reaction equation

HRID 972707 reaction equation
ClC1C=C(Cl)C(Cl)=CC=1O[C:11](=[O:18])[C@@H:12]1[CH2:16][CH2:15][C:14](=[O:17])[NH:13]1.[NH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24].ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C>CN(C)C=O>[NH:13]1[C:14](=[O:17])[CH2:15][CH2:16][C@H:12]1[C:11]([CH:22]([CH2:21][CH2:20][NH2:19])[C:23]([NH2:25])=[O:24])=[O:18]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 186154-AminobutanamideHCID 757711-HydroxybenzotriazoleHCID 1111082,4,5-Trichlorophenyl 5-oxo-L-prolinate

Product 1

HCID 86735131L-Pyroglutamyl-4-aminobutyric acid amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.9 g (12.65 mmols) of L-pyroglutamic acid 2,4,5-trichlorophenyl ester were added to a solution of 1.76 g (12.9 mmols) 4-amino butyric acid amide and 1.72 g (12.75 mmols) of 1-hydroxybenzotriazole and 1.65 ml of N-ethylmorpholine in 40 ml of dimethyl formamide. The solution was allowed to stand for 1 hour at room temperature. It was concentrated and triturated with ether. The substance was suction-filtered and chromatographed in methanol/water (1:1) through Serdolit Blau. The eluate was concentrated and the residue was triturated with ether and suction-filtered.

Workup

  1. concentrationIt was concentrated
  2. customtriturated with ether
  3. filtrationThe substance was suction-filtered
  4. customchromatographed in methanol/water (1:1) through Serdolit Blau
  5. concentrationThe eluate was concentrated
  6. customthe residue was triturated with ether
  7. filtrationsuction-filtered

Sources & evidence

ORD record
ord-99c8a129abd1453e801d533d1ba8d348
Source dataset
uspto-grants-1977_10
Patent number
US04053588

Reaction notes

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